Podcast Description

You start dating again, but start to have some serious questions: Are you ready? Are you moving too fast? What about S-E-X? Are you being taken advantage of? When should you walk away? When should you bump things to the next level?

In this interview with mental health professional Helen Keeling-Neal, we explore these dating questions and more, providing some first hand tips and guidance on how to, when you are ready, successfully navigating your transition to dating again and developing a healthy, next relationship.

Interview Highlights

Helen 5:15
The widower may be subconsciously looking to fill a nurturer role in their family, especially if there are kids, and you could be thinking that maybe bringing in someone to take over that role, if that was a traditional sort of role that the wife or partner held in the family system.

Helen 6:30
And you know, I think one of the big things is you have to check in with is what part of your body wants this relationship? Where is it based? Are we based in “Hey, I would like to have sex, I would like to be sexually intimate with someone, I crave that”. Well that’s a normal human, wonderful thing to have in one’s life. And here are women who want to be with me. That’s very engaging, very attractive, very validating for someone who may have been with someone who was ill and not able to engage that way. Or someone, a widower, that has had their self esteem knocked down as a result of a really difficult time through the loss. It can feel good to be found attractive, right?

Tom

And my first piece of advice would be to take it really slow. Go on those coffee dates, but don’t immediately go out to a romantic dinner, where A can lead to B can lead to C, and then you’re doing things maybe too early. I think that taking it really slow is good. Because you need to find out where you’re at in it. You may not be ready. Or you may find out that they aren’t ready for everything that you need in a partner, because as widowers, we have some special needs. And there will need to be some special nurturing, and honestly a special person or two that needs to come into your life to help you through that healing process.

Tom

And then my other piece of advice is on sex. If we can go back to that topic, probably put it off longer than you might think you would have when you were younger and dating the first time, maybe in your 20s or 30s. I do think that it’s hard to make a good judgment about your partner when sex is involved. I think it bonds us as men and women in a very special way. And my advice would be to set up some pretty strict boundaries where if you want to go and have a fling, and this other person wants to have a fling, and that’s the mutual understanding: That’s how you do that. However, if you’re looking for a deeper relationship with this person, I would definitely encourage putting off sexual relations longer than you normally would have.

Tom
And I think that can sometimes take time for people to understand that it’s not a quid pro quo on “I love you” or commitment in the relationship. In a healthy relationship, there is no quid pro quo, You’re doing the things you want to do for them. And they are the icing on your cake, not the whole cake.

Tom
One of the things that I think is really important are things like the moving-in, the financial entanglements, the business dealings. I think too often, nowadays, whether it’s widowers or even just general relationships, I think people get involved at that level, much too soon, perhaps. Maybe where the commitment isn’t quite completely agreed to yet, all of a sudden, there’s a financial entanglement or business entanglement, or perhaps a family entanglement that occurs when perhaps should have been delayed, and there should have been more of a commitment.

Helen
I don’t want anybody to be victimized in this financially, emotionally in any way whatsoever. We don’t want someone to give up their home and then be left with nothing as well. You know, so it needs to be a consideration in place and not feel uncomfortable, or build up resentment and things like that, that all of a sudden end in an explosion. And oh, “what the heck just happened?” kind of thing.

Helen
We have to remember, if you’re in a relationship with someone who has been through a divorce, there is grief there that can be very difficult. We have to remember that we don’t have a corner on the market on grief and loss.

Helen 45:08
Know yourself first.

Then, get to know your other person and take your time with it. Ask the hard questions and have the difficult conversations. Even if you’re afraid to push the other person away. If you do it, know that if it doesn’t work out, you will have more opportunities and lovers out there, it will come to you.

Tom Pisello 

My guest today is Helen Keeling-Neal. She is a licensed mental health counselor, a licensed Marriage and Family Therapist and a nationally certified counselor with a private practice in my hometown of Winter Park, Florida, as well. We’re proud to have Helen on the board with us here at growth through grief and she helps guide our practices on all things concerning the mind and mental health. 

And, Helen has personal experience with grief and loss herself, unfortunately, as a widow, with her husband passing away when her children were only four and six years old. 

And we are here to discuss Dating. I know there was another prior episode on dating, but there were so many aspects of this important topic that Helen and I needed to add another session. 

So Helen, welcome back.

We left off on the dating continuum, where things were starting to get going. And we discussed dating apps and things like that.

I know a lot of widowers, they get reach outs from women pretty early on, how do you deal with those reach outs?

Helen  2:11  

Yeah, that can be a little complex. There’s a certain vulnerability that someone is going through after loss. And then on the flip side of tha  is the fact that the widower would like to be cared for in a relationship. 

So what you’re talking about, in particular, is when a widower becomes sort of, on the market, so to speak. I don’t  love that term, but they’re now available. And there are people who would like to date this person, and are making overtures to get to know them. 

Tom 2:30

And some of some of those Helen might be good reach outs that are positive. And truly, they want to get to know you better. They want to have a great relationship with you. 

Others might not have those same intentions, and maybe a little bit more selfish and not reaching out in a caring way, but maybe reaching out in a selfish way, and perhaps a way to take advantage of a widower. 

Helen 2:45

And there was that vulnerability that goes along with having a loss right afterwards. And I think too, one of the ways that I think widowers can be particularly vulnerable, is when someone comes in through the side door of caring and helping and nurturing.

This may not necessarily be conscious on someone’s part, they may feel like they are caring and nurturing. But then may also know that this is an eligible person, that fits a criteria or a lifestyle or a connection that they’re missing, and especially if there are people who may be known for being affluent, and now at the same time, are particularly vulnerable. 

You have to have much more discretion with choosing who you’re going to get connected with, just to make sure it’s done from a place of integrity.

Tom 4:22  

And to be sure you’re not just trying to medicate with a relationship, right? I know, a lot of widowers were lonely through the grieving process. For many, that started while their wives were sick and ill. Perhaps if it was a long illness that led to the passing. 

While for others, where it’s shorter, they might have a hole that they’re looking to fill and can then become victims of someone without noble intentions, and perhaps with even direct intentions to take advantage of the widower

Speaking to folks at the Modern Widows Club. I don’t know if you faced this, but women can be seen as pretty vulnerable in their loss. And there are folks that are looking to trick and deceive. And so we do need to have discernment.

Helen  5:15  

Very much so and vice versa, you may find with widowers.  

They may be subconsciously looking to fill a nurturer role in their family, especially if there are kids, and you could be thinking that maybe bringing in someone to take over that role, if that was a traditional sort of role that the wife or partner held in the family system. 

And with the widows we often see a real financial insecurity in the loss. And so sometimes the widow is in a position where they’re looking to help fill that role of a provider. So the teeth sort of fit in there on both sides. 

Tom  6:05

Now, if it’s someone that you are interested in, where there is now an opportunity and enough time has passed. So you’re comfortable and you’re feeling secure in going out there.

How do you begin that vetting process? 

Can you outline the things you think you should look for in yourself to be sure that it’s ready for a healthy relationship, as well as perhaps what you look for in the partner that is actually going to form a healthy relationship and gets the relationship off t on the right foot? 

Helen 6:30

Yeah, well, we talked about this a little bit in the last podcast. We talked about knowing what you want, first, and knowing who you are first. 

And you know, I think one of the big things is you have to check in with is what part of your body wants this relationship? Where is it based? Are we based in “Hey, I would like to have sex, I would like to be sexually intimate with someone, I crave that”.  Well that’s a normal human, wonderful thing to have in one’s life. 

And here are women who want to be with me. That’s very engaging, very attractive, very validating for someone who may have been with someone who was ill and not able to engage that way. 

Or someone, a widower, that has had their self esteem knocked down as a result of a really difficult time through the loss. It can feel good to be found attractive, right? 

And then being wary of setting up a relationship based on these elements and finding that the relationship doesn’t have the substance of the legs to go along with it. And ending up hurt or hurting.

There’s a need for discussion when you meet someone and when you start dating someone.  Not right away, because,right away, that would just be weird. But there’s a need for discussion on what is wanted. What do you want? What are you looking for in a couple ship? Are you looking for a friend to hang out with and go to the movies with and have sex with, or are you looking to really develop a coupleship.

And so that’s important to happen. 

Tom

I think that being able to have those open discussions, as you said, maybe not in the beginning – not the first couple of coffee dates but soon enough. 

And my first piece of advice would be to take it really slow. Go on those coffee dates, but  don’t immediately go out to a romantic dinner, where A can lead to B can lead to C, and then you’re doing things maybe too early. 

I think that taking it really slow is good. Because you need to find out where you’re at in it. You may not be ready. Or you may find out that they aren’t ready for everything that you need in a partner, because as widowers, we have some special needs. And there will need to be some special nurturing, and honestly a special person or two that needs to come into your life to help you through that healing process. 

And then my other piece of advice is on sex. If we can go back to that topic, probably put it off longer than you might think you would have when you were younger and dating the first time, maybe in your 20s or 30s.

I do think that it’s hard to make a good judgment about your partner when sex is involved. I think it bonds us as men and women in a very special way. And my advice would be to set up some pretty strict boundaries where if you want to go and have a fling, and this other person wants to have a fling, and that’s the mutual understanding: That’s how you do that.

However, if you’re looking for a deeper relationship with this person, I would definitely encourage putting off sexual relations longer than you normally would have. 

Talk about your views on it, Helen, as the professional.

Helen  10:00  

Well, everybody’s different in that what is right for somebody to put it off may make your partner feel like they’re not attractive. But that’s an opportunity to work through that. 

But I think really what is really great is when you’ve had these conversations, you’re dating someone, you’ve had these conversations and you decide you’re gonna give it a shot. And you want to develop the relationship and come up with a timeframe together to do just that

So if it’s 30 days, or if it’s going to be longer, you come up with that timeframe together.

Tom  10:34  

And this is your goal to get to know each other and be mindful, be specific about how you can get to know each other, what kind of questions you’re gonna ask.

Helen  10:42  

And also, it’s kind of fun, because you know, you’ve got this delayed gratification down the road. And you know, when it happens, you’re in it together, you’ve already spent this time getting to know each other, knowing that this is down the road, which is exciting.

Tom  10:58  

And then you can have that experience together, which can be great. And again, you decided about how long, and it was mutually agreed to, so there is not a sense of rejection, where it could be like, “Oh, well, she’s expecting it from me, but I’m not ready and she is upset as a result”.

Helen  11:16  

That’s why conversation is so important. And you know, that when you have sex, you start to find out whether you’re compatible there too, because that’s a process as well. Not everybody is compatible, sexually. 

Tom

Now something that you deal with later in life, in terms of, your sexual relations, is testing, and making sure that you and your partner have both been tested? For things that we haven’t thought about in 20 or 30 years? You may not necessarily need protection, when you’re older, perhaps, you you’re fixed and your partner is through menopause. And so pregnancy is less of an issue, right? But then we find that older people, particularly, there is a wave of STDs in a lot of older communities. 

So talk about that a little bit and some things we need to consider there. 

Helen

So you know, you want to have those frank conversations. 

If you’re someone who carries the herpes virus, you want to be able to have that conversation with your partner early on, before you’ve been sexually intimate. And to do it without shame. 

That’s a very, very, very common thing. It’s very normal.There isn’t the shame stigma around it that they used to be. 

You also want to discuss protection, and you want to discuss birth control, because there are a number of the widowers who are of the age where pregnancy could be an issue.

Tom  13:00  

And you just need to be frank, You need to talk about your sexual health and continuing that sexual wellness for you and your partner. I want you to remember that both people in the partnership are responsible for their own sexual wellness.

Don’t rely on your partner for that, right? 

Helen

Correct. Yes, yes, you really have to be responsible. You really do need to bring up those conversations. You do need to ask the questions about if this person has any STDs, and when was the last time they got tested? And all those kinds of things that go along with it are really important. 

And as adults, you know, we’re in a culture that does not promote this. So it’s just effing awkward. Let’s face it, to sit down and say, “Hey, let’s have some adult conversations about a really awkward topic. Okay .. I’m going to start and let’s talk about STDs”. 

And then just start it from there, saying it sort of say it lightly, and use that as your entry. And if you’re talking with someone who is unable or unwilling to have those conversations…. uncomfortable is fine, of course, they’re going to be uncomfortable. That’s a bit of a clue for you though if they are unwilling or unable.

The fact that this is someone who may not be able to open up and talk freely about what needs to be spoken about in relationships and indicates that this relationship may not elevate to have good communication.

Don’t back off. You can circle back around to it. If it’s too uncomfortable, right then for the person to have the conversation with, but don’t do anything until there’s been resolution and clear communication about it. 

Helen  15:00  

Healthy sexual health is not necessarily about being STD free. It’s about communicating and protecting oneself and one’s partner by communicating. 

Tom

I can tell you firsthand that testing is available – it’s easy to quickly get this done together. And so, you know, saying to your partner, hey, I’ll test you test to make sure we’re going into this right, you know,

If you were sexually active before, I think is a great way to really reach that mature part in your relationship. And I think if you’re the one bringing it up as a widower, there’s a transparency and an honesty there that I think your partner will really respect, that they may not have gotten from others. 

So Helen, we begin to get into a relationship. And, as a widower, and as a widow, I think you face this as well, it’s really easy to and it takes a long time to get over triggers, right? Very easy for us, when there’s been this level of hurt and loss in our lives. Perhaps things that haven’t fully been worked through, that we’re going to get an amygdala hijack? And te four F’s come into play, talk about those and how they might manifest themselves in the relationship as we get in after the first few dates.

Helen  16:28  

We talked in the last episode about my experience on triggers, and this was smelling the “wrong” cologne. The wrong cologne wasn’t the wrong cologne. It just wasn’t my late husband David’s cologne, right? 

So that’s an example of my limbic system being hijacked by a memory. But there are so many other things that may make someone feel like running away. So simply driving in a car with someone new, and a song comes on that’s particular to you. And as men, culturally you are programmed to not cry, certainly not cry on a date. So maybe you’re fighting down the tears as the song is coming on. You have a couple of choices, then.

You can say, if you know the person well enough, “I  feel some grief right now. Because this is a song, my wife and I used to listen to when we would drive to the mountains. So it’s making me feel really sad. I’m happy I’m here with you. But I’m feeling really sad about this song”. 

And so again, it’s about the communication with your partner. And it is about the communication with oneself and acknowledging the truth of what’s going on. It’s not driving to the restaurant and chugging down three shots of tequila, because you don’t want the grief to come up, or eating an entire apple pie. It’s not jumping into bed, let’s have some hot sex as a way to shut it down. I mean, all of that can be good when used mindfully and in moderation.

There are just so many triggers, so many things, a sentence or word, a lock, an article of clothing, a color. And it’s going to happen all the time. And acknowledging it…acknowledging how you feel about it and verbalizing it is really important. 

And you can have that conversation with your person and you can say to them, “Hey, this is part of the grieving process. I want you to know when that happens to me, and it is going to happen to me and I don’t always know when it’s going to happen. That I want you to know that’s nothing to do with you. And that I want to be with you. It’s simply part of the grief process”. 

Tom

So the four reactions that have been most common with me in this have been Fight where this anger that comes up, like almost out of nowhere, and it’s a little outsized reaction to maybe something that someone says and it has nothing to do actually with what this person said, but it’s .triggering something from the past. 

One that I know you experienced, which is Flight…Maybe you know someone who just triggered you the wrong way or triggered something in the past. Or someone says something wrong and you just want to run and leave the table. 

Freeze is one that a lot of people face where you just want to crawl up in bed, in a ball and cry or where you just shut down when someone will say something wrong and all of a sudden it’s like, blank … a blank look on your face, your inside yourself. You just don’t want to hear anything that person said. 

And then, Helen, there is one that I didn’t even realize was impacting me. But Fawn mode. Talk about that a little bit, because that’s one I don’t think everyone fully understands. But it’s actually a fairly common manifestation for men in particular for widowers. 

Helen  20:30  

So we’re talking about the sympathetic nervous system, which is the Fight and Flight, and then more the parasympathetic nervous system, which is the Submit mode of Freeze and Fawn.

So with Fawn and more of the Submit, it’s about your “Yes, dear, yes, dear” … You’re going to go out of your way emotionally to make it okay with this person, as a way to avoid what’s really going on underneath. If I can just make this okay, in this relationship, everything will be okay, I won’t have to feel these feelings. 

So everything is about the other person and making the other person happy. And submitting to their desires, taking on full responsibility for it being messed up, or not going well. And just giving over your power, you’re basically turning over your emotional power to that person without even realizing you’re doing it. 

Because you’re thinking you’re nurturing and caring and giving. And then what happens? You end up depleted and what happens is, all of a sudden, you’ll realize what has happened and have an outsized reaction to that and saying, That’s it, I won’t be taken advantage of anymore. 

And the person is looking at you like, What the heck just happened? You were pleasing me all this time? Yes. Yes. Yes. Yes, giving, giving, giving, giving, All the time, your boundaries were being overstepped yet you didn’t step up to the plate, and let them know that that is your fault, not their fault. 

Set the boundaries. It’s like a child that acts up and you don’t set boundaries, and then all of a sudden, you whack them, which you can’t do. But that’s ultimately what the reaction becomes is all of a sudden it becomes the lion. And there’s this reaction, your fight. The flip eventually kicks in to the sympathetic nervous system. Because that self abandoning form and submitting leads to resentment building up, what about my needs? You never? You always?

Tom  22:31  

So I highly recommend, for those who think they recognize a little bit of this, where you’re the pleaser, you’re the doer, you’re the giver. And you’re feeling that resentment starting to build up Here’s two essential books that I read to help overcome that. 

One called Beyond Boundaries. And the other one, I highly recommend no more Mr. Nice Guy, now this last one has a bad title, a controversial title. But it actually is a very productive book. 

It’s not about being an asshole. It’s no more Mr. Nice Guy, don’t be a fawn forever. And by setting boundaries, you’re actually doing the relationship and your partner more benefit than what you might know. 

So both of those are listed on our website, under the Tools section. Highly recommend both of those, 

Helen any that you recommend, with regard, I just recommend anything that Brene Brown does around the shame component of this, because I think there is a shame component in there, where we’re giving away in order to give to so that we can get this sort of underneath, secondary gain. If we are caretaking everything, then maybe they won’t leave. Or maybe it won’t end. So I think Brene Brown has a great way of helping people learn how to value themselves and understand that boundaries help both of us in the relationship, both people in the relationship, because the other person when that flip happens, and they’re like, Well, I didn’t know that you didn’t like mustard on your hot dogs. Why didn’t you tell me?

Tom  24:16  

Exactly. And then that becomes your issue. You know, it’s not that person’s not reading your mind. It’s not their issue, it’s your issue because you didn’t set the boundaries and you didn’t let them know what you want. And so that’s your responsibility.

It actually does help the relationship and benefit the other person by doing that. And they will learn to love and respect you a lot more rather than just feeling like you’re the giver and maybe they can walk all over you kind of thing. So really important. Both those books, can give you the education. 

Helen, dating isn’t something that we’ve done in a while right as a widow and widower. We didn’t expect to be in this situation. At this point in our lives. We were in a relationship for a really long time.

Helen  25:00  

Where it was, hopefully a positive communicative relationship, where these things weren’t as big an issue. And now we are getting out there in the dating world, it’s going to come at us a million miles an hour. And we need to be prepared. And we need to educate ourselves. 

So definitely doing that research and being prepared, knowing fight, flight, freeze and fawn… knowing how to make sure you’ve done the work so that you’re not reacting in these triggered ways, or not falling into one of these personas, I think is important.

Tom 25:30  

All right. So things are going well. Now, a couple of a couple of things. I’m going to go through a few of these with you. So we’re not going to dive too deep into each one. But the first thing is, you’ve been dating someone for a while it’s going well, you’re also maybe going out on a couple of other dates with some other people. Um, when is it time to make a commitment?

Helen 25:54  

And what does that look like? Define commitment?

Tom  25:58  

Yes, and I think that’s part of what you need to do, with the other person, right. So talk about that? 

Helen  26:08  

Well, I think there are varying commitments and commitment styles and commitment ways. One may be as exclusive, we’re not going to be dating anybody else.

You know, we are in a monogamous relationship or a polyamorous relationship, there are people who practice ethical polyamory, right. So, you know, you want to decide in these little steps, what the commitment level is.

There’s no rush, usually. Now there is a difference, though, there’s a difference between us Tom at our ages, we have a different point of view than someone who may have not lost a spouse or not have children and wants them, or may have very young children, you know, they’re on a sort of different developmental track on where they are in their life. And so we have to remember that someone may want to accelerate a little bit and and may want to marry sooner or move in sooner or commit sooner because they want to raise a family, or they want to have a family unit to raise a family.

Tom  27:19  

Here, too, I think that doing some work in this area was really important for me. 

I think understanding that you’re on the same page with who you’re dating is the most important thing. So you’re ready for that next step, communicate that next step to your partner, you don’t leave it up for guessing, because you might think you’re at that next step. 

And they’re not even close to being there, or vice versa, which tends to happen a lot more with widowers, where the women that at least I’ve dated, have thought that next step was already there. And maybe it was, maybe it wasn’t, but we hadn’t talked about it. 

And so you’re assuming a lot, or you’re trying to have your partner read your mind. And I think that that can be a challenge. 

So I think being really explicit about the purpose of where you’re at in that relationship, the commitment that you’re willing to make, and that they’re willing to make is important. And the book that helped me a lot here was a book called Getting to Commitment. Another one that we got on our recommended reading list that I highly encourage. It’s one of the first books to read about dating. And it really helped me a lot to understand all of the challenges and how they show up. 

If you don’t have these conversations, and you should spend time every week, if you’re in a relationship that’s gone beyond, you know, the coffee dates, and now you’re dating, you’re spending time with each other. And then spending a little bit of time each week, religiously talking about the relationship, how’s it going? How are we doing? Are we on the same page, you know, and not maybe using those exact words, because I don’t think those words come out of my mouth too often. 

But getting at that with your partner is essential. Yeah, checking in. Another thing I think that’s important to remember is, a lot of the time you’re not going to be on the same page. So what do you do with that piece? 

Helen

Someone else needs time and space to grow into that commitment. You may be ready for it, they may need to do some personal work to become ready for it. Yeah, and vice versa. 

And that’s not a relationship at that point. No, unless you want it to, you’re looking for right then and there to be at that point, but that just means okay, I understand where you’re at you understand where we both would like to get this I think some of the understanding the destination you’d like to get to, but also having understanding of the reality of where you’re at and where they’re at. 

It’s like that big thing of saying “I love you” who’s gonna say at first and is somebody’s going to respond, but I’d like to empower people to say it because they feel it Yes, without an expectation of a response or an equal verbal response to it. 

Tom

And I think that can sometimes take time for people to understand that it’s not a quid pro quo on “I love you” or commitment in the relationship. In a healthy relationship, there is no quid pro quo, You’re doing the things you want to do for them. And they are the icing on your cake, not the whole cake. 

Two important things that I remember now that I can’t say I got right through maybe the first couple of post relationships. Okay, the commitment is there, it’s going well, you’re monogamous to each other. You both understand that you’re in a relationship. And now it’s time to take it to that next level.

That usually involves some entanglement which could be done in a good way, or could be done in a bad way: things like moving in, like starting to financially entangle, maybe with cars or homes, maybe joint business dealings and working together. That’s a whole other different level of commitment. Talk about those things, Helen…

Helen

I’m just noting, that’s an interesting word that you use “entangle” versus “blended”.

Tom  31:11  

Which to me has actually a positive meaning.  it’s derived from the term quantum entanglement and how it goes … you have these entangled electrons, where you flip the rotation of one and over a great distance and instantly, it flips the rotation of the other to match. Yeah. So a simpatico entanglement, not a troubled one.

Helen 31:37  

I like that. That it’s a scientific reaching and  finding. Yeah, a lot of conversations there. 

So when we’re talking “next level” of commitment, we’re looking at things like going on vacation together. You know, who pays for it,  how would we do that? Do we take kids if there are kids? If so, where do we go? And then we traveled together, how many rooms do we have? Do we share a room around the kids blah, blah, blah, all this kind of stuff. So you’ve got to have conversations about that. What works when you’re dealing with children who have lost a parent, is really, really important. When you’re doing something like a vacation or a family event for the first time together in this new format with a new person. There’s a very difficult thing for children many times because they can feel it not like a game, but like a loss or missing or an absence of mom or an absence of that. So you want to be mindful about that too.

Tom  32:45  

I think one of the things I feel a lot, Helen is that the kids feel like they could maybe lose me to this other relationship or maybe to the other family.

Helen  33:01  

Yeah, because it makes everything different. And again, if it’s going to be a blended family, with other children, you’re looking at who might have been the first born in your family is now the second born in a blended family. So there’s a complexity to it. So therapy can be really helpful. For kids in this, you know, I’m a big fan of New Hope for grieving children and family, that can be really helpful there because it can normalize it for the kids.

And even doing this with your new configuration, some family sessions, even though you’re not technically necessarily married, but just to get some resources and maybe talk through some things and some tools with a family therapist who can help.

Early on, well, not that early on. About a year and a half after David died, I had a relationship with someone, and he had children. And I’ll just never forget one time, the little boy saying to me, we’re at the beach, and we’re on vacation. And for the first time, all of us together, saying to me about how he didn’t know if his dad had told me that he was having some very big feelings about this. Yeah, his parents were divorced and he was having some very big feelings about this. 

And I just remember sitting there and like in the water with him and being like, Well, yeah, that makes a lot sense that you would have some big feelings about this. It’s kind of hard. It’s hard right? Then just being able to give that to him. Number one, how awesome is this kid for expressing that? And how lucky am I that he felt comfortable enough and safe enough with me to say it? 

Tom

And how jealous I am that you’re a therapist, and the advice that you give at that point in time, wishing that we all could have your wisdom..

Helen  35:25  

And here’s the thing, this was before I was a therapist, I wasn’t a therapist, 

Tom

I think you were to do this, based on that answer. That was wise of you. 

And I think a lot of times the kids are just wanting to be acknowledged, wanting to listen to wanting to feel like they’re heard, and that their feelings aren’t just pushed aside. 

And it takes an extra bit of patience and awareness, I can honestly say that I’m on the go so often, that I was reminiscing that many, many times in my relationship with my kids, just saying, “get with the program”. And this is, even before Judy passed, It was always “get with the program”. 

Helen

So it’s not like anything has changed. But you really need, I think, to spend that extra time and being aware that they are going to have those feelings, even if they didn’t express it, So you’re right. Tom, I want to tell you, though, I want to say that I was on the flip end of that, where I was too much about the feelings, I was to sort of indulging the feelings and that kind of point of view that I came from. 

So you know, it works on both ends of the spectrum. And that created problems too. Because then the child who doesn’t maybe know how to accept this new relationship is throwing a tantrum, but say, to the extreme, right, and you’re coddling them about their feelings. And it’s all about their feelings, and nothing about what may be good ultimately, for the family. 

Tom

So I completely agree with that. One of the things that I think is really important are things like the moving in the financial entanglements, the business dealings. I think too often, nowadays, whether it’s widowers or even just general relationships, I think people get involved at that level, much too soon, perhaps. Maybe where the commitment isn’t quite completely agreed to yet, all of a sudden, there’s a financial entanglement or business entanglement, or perhaps a family entanglement that occurs when perhaps should have been delayed, and there should have been more of a commitment. 

Maybe you need to be engaged before you move in. Or maybe there should be some form of bigger discussion agreement and validation that occurs before you’re getting into a business partnership or other things like that. Right?  Talk about that a little bit and how important that is. 

Helen

Yeah, it’s almost like you need a forensic analysis of the finances, of how we’re going to choose the furniture. If you’re moving into maybe the widowers house, what can this person coming in change in the house, so that it’s going to feel like their home versus them living in another woman’s home?

You know, this really does warrant a lot of question and answer sessions to really get down to. So how do you feel about this? And what if this, it’s quite difficult, and it can feel very complex and overwhelming, but it’s just an indication to not jump at it. 

Just take some time, diligent communication, and having that, I think in the beginning, so that you’re having these little conversations that build and build and build into this mutual agreement, alignment kind of thing. Even if they’re not in total lockstep all the time, which they won’t be.

Tom

If you’re totally simpatico with someone all the way, I’d start to doubt where they’re at and where you’re at. 

Sometimes there’ll be the pause button that gets hit. And the book Getting to commitment talks about that sometimes you just need space, and they need space. But as you start to get into this relationship more, I think you need to have these agreements in place. Sometimes legal ones, sometimes bigger commitments, but actually get it to where things aren’t left up to chance that you’re just doing something without a mutual expectation and agreements so that it’s clear that when one person doesn’t fulfill on their end of it, that there’s not this big surprise that comes out of nowhere, right? 

Helen

I don’t want anybody to be victimized in this financially, emotionally in any way whatsoever. We don’t want someone to give up their home and then be left with nothing as well. You know, so it needs to be a consideration in place and not feel uncomfortable, or build up resentment and things like that, that all of a sudden end in an explosion. And oh, what the heck just happened? kind of thing. 

So with that piece too, I think it’s really good for a couple to sit down and say, because usually I would think, Tom, you have met people who are divorced who have had previous relationships, probably not so much widows. Right? And so if you’re with someone who’s divorced, you want to have a conversation about how were finances handled in your previous relationships… what worked from that, and what didn’t work from that. And what do you think you would want moving forward? And then vice versa? How were your finances over here handled? What do you think we need moving forward with a certain amount of autonomy you know, and then a certain amount of combined resources? And just having that discussion, You might have someone who’s a saver, and you are someone who is like, carpe diem, let’s get a windsurfer. We’re going to Italy. That’s me.

Tom  41:03  

Helen, there’s a lot there. I think that you’ll find, if you don’t have the discussions with your partner, especially if they have been through a divorce, which isn’t an easy process for anyone to go through, where you may have triggers there if you don’t address these things, there’s certainly your triggers to worry about, but theirs as well. 

And it’s complex at our age, you know, with their children there, there are things to think about and their well being to think about … college education, things like that. 

And, making sure you’ve got a financial report on the other person, make sure you clearly understand what you’re getting into with them. What is their credit report? How could that potentially hurt or help you through things? 

And, then you’re ready for that next step, and remarrying if that’s an option for you. Something that you thought about and you want with that person. Talk about that a little bit. 

Helen

Yeah, I’m going to back up a little bit, and then we’ll talk about that. Because I think really, when you coming up to the marriage line, you want to know the person emotionally, physically, financially, and spiritually, these are the areas you want to really get to know each other. 

Then there was something that you said that really activated something. We have to remember, if you’re in a relationship with someone who has been through a divorce, there is grief there that can be very difficult. We have to remember that we don’t have a corner on the market on grief and loss.

It’s a specific kind of grief and loss through death. But there is grief and loss and complexity and a whole bunch of stuff that goes along with divorce. So we have to be very mindful, because that can be inside one’s head that little bit. Well, you know, they’ve got some help from this person over here, their ex,. I don’t have any of that. We want to make sure that loss, 

Now remarrying…. Let’s go onto that topic now…. and then we all live “happily ever after”. That’s just the way it goes. Yeah. Wouldn’t be awesome. That’s a Princess life.

So who do you invite to the wedding? Do you invite your in-laws? It’s complex in that sense. But I think what’s so important here, if you make a decision to remarry, You want it to be fresh for you as a couple. You don’t want to do anything that is the same in the past on either side of the relationship. You want to craft something that works for you. Now, you want to plan it in a way where honestly, you could giggle with joy about eating cake, and you know, really have it be fun and not stressful, and just make it completely about the two of you.

You have to remember that remarrying will have an effect on the children and it will also bring up grief for both of you. If the person is divorced, or the person has had a death, because you’re going to be thinking about your previous marriage, but you’re also  going to be thinking about them completely differently. So you need to be aware of that, that the grief might pop up.

Tom  44:30  

Yes I totally agree. I think you had a good point there Helen, making sure you’re creating something special and unique going forward. And I think that’s throughout the relationship as well not trying to recreate what you had before…recreating that prior relationship just because it worked. Making sure you’re going to those new locations, creating new and different memories. I think memories are important. Helen, what’s the one piece of advice around Dating – Part Two, that you’d like to leave our growth warriors and widowers with today?

Helen  45:08  

Know yourself first. 

Then, get to know your other person and take your time with it. 

Ask the hard questions and have the difficult conversations. Even if you’re afraid to push the other person away. If you do it, know that if it doesn’t work out, you will have more opportunities and lovers out there, it will come to you. 

Tom

Yes, I agree completely. Helen. Have those conversations, because they will either make you stronger as a couple, even if the pause button will get hit a few times by doing that, or it will let you find out rather easily and quickly that “you know what, this wasn’t for me”.

Helen  45:57  

So absolutely. I think communication is key. 

Tom

Three resources that I loved: Getting to Commitment, Beyond Boundaries and No More Mr. Nice Guy. 

Brene Brown, that Helen recommended. Helen. I’ll get those books up and listed in our resources as well because I know that’ll be important. Our growth warriors / widowers love to grow and have a growth mindset. So hopefully they’ll go and consume those books. And I know they were educational for me and I took great things out of all of them. 

And the Brene Brown series is a good one as well. She always has really, really good advice. 

So Helen, thank you so much. We’re gonna have you back as a guest to cover some other really, really important topics!

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The information in this podcast is for informational purposes only. No material on this site is intended to be a substitute for professional medical, mental health or spiritual advice, diagnosis or treatment. Always seek the advice of your physician, mental health counselor, spiritual advisor or other qualified health-care , mental health or spiritual provider with any questions you may have regarding a medical condition, mental or spiritual challenges or treatment. Before making any changes to your health-care, diet, exercise or other aspects of your life, please seek professional advice, and never disregard professional advice or delay in seeking it because of something you have read or heard on this podcast or through other Growth through Grief resources.

About The Host

Grow Through Grief Founder

Thomas Pisello

Growth Evangelist / Growth through Grief Founder

Tom Pisello is a widower and the father of two daughters. Tom lost his wife Judy in 2017 after her ten year battle with cancer.

Tom founded the Growth through Grief site, resources and ministry to help share his personal experiences to grow through the grieving process, and to share with others to help in his own and other’s healing process. Through this process, Tom gained his sobriety, lost 60 pounds, gained a growth mindset and rekindled lost faith, now sharing these hard-earned lessons and the lessons of other widowers and experts with you.

Prior to creating Growth through Grief, Tom was a successful serial-entrepreneur, analyst, speaker, and author of the business books Evolved Selling and The Frugalnomics Survival Guide. He was well known as “The ROI Guy”, founder of Alinean and Interpose, a Managing VP of analyst firm Gartner, Chief Evangelist for Mediafly and founder of the Evolved Selling Institute and host to the popular sales and marketing podcast – Evolved Selling