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Choosing Between Your Ex and Your Boyfriend - Relationship Advice

Updated on August 13, 2010

Dear Veronica,

Veronica, I wrote you once before (not being a bridesmaid in my sister's wedding) and we've had some interesting exchanges in the comments. I'm hoping you can give me more insight again. I think I'm just stuck in the middle of a situation that I can't quite see clearly and I'm hoping that you'll be able to shed some light on it for me. So here's my situation...(I apologize in advance for this being so long)

I'm currently in a relationship with a wonderful man. He's 25 and I'm 31 and we've been dating for 1.5 years but were friends for almost a year before that. We moved in together 4 months ago and it's been great. Not perfect by any means, but really, really good. I have a strong connection with his family, especially his mom, and my family really likes and respects him (which is no small feat as they're considerably more difficult than his family). I'm continually impressed with what an amazing person he is, especially his ability to work through difficult emotional situations constructively (I wasn't nearly that evolved at 25). 

We've had a couple challenging situations lately---not so much relationship-wise, but life-wise. He lost his job a few months ago and has since then decided to try to start his own business. He's been working very hard at it (it's internet-based) and is a very smart guy. I believe that it is inevitable that he will be successful, but I'm not sure when that will happen. Even in the best case scenario, we won't see any revenue generated for several months at the very least. Unfortunately, I just got laid off a couple of weeks ago and now our safety net of my income is gone. This has stressed me out considerably (he seems a little more zen with it). We both have some savings, so we're good for at least 6 m onths or so, but it definitely unsettles me and makes me anxious, especially as I had a long period of unemployment in 2008 when the market crashed which ate up the vast majority of my savings. I'm sure I'll find another job in that time frame as the economy is better than it was in 2008 and 2009, but until then, I'm anxious about finances.

I've also had a rough time with family related issues in the last six months or so. Not surprisingly, my sister's wedding brought up a lot of long-standing issues for a lot of people in the family and it didn't end up being the happy experience and memory for everyone in the family like my brothers' weddings were. Probably me and one of my sisters-in-law were the most hurt by some of the things that happened. But they weren't really anything new---the wedding just highlighted some things that have been contentious and hurtful for years. I highly doubt things will change any time in the near future, if ever, so I should be used to i t now. But I guess it's just always hard to accept that your family isn't quite who you wished they were (or at least, that's a battle for me). 

Additionally, before I lost my job, we'd been discussing marriage a lot. It's the not uncommon, I'm ready and he's not quite there yet. Especially considering our age differences, this is no big surprise. But with the work situations being so uncertain, I suggested tabling those discussions until I find a job (the financial uncertainty doesn't seem to affect him as much). He happily accepted that suggestion as he's not the one that wants to get married sooner rather than later. Plus, I think that we're both able to recognize that we've got a really good thing right now, feel grateful that we're in each others' lives and love each other incredibly. It's a lot of background, but I wanted to let you know the lay of the land as I believe there are multiple pressures on us as a couple and individuals between our financial situati ons, my family and our commitment expectations. So, here's the actual issue...

Four months ago or so my ex contacted me (after about a 1.5 years of not speaking to one another) and wants to see if we can be friends now that more time had passed. It had been about 2.5 years since we broke up. We'd been together for 6 years or so, we were extremely close (or so I thought) and it ended badly. There was some betrayal and infidelity on his part that absolutely devastated me. But more than the loss of the romantic relationship, I grieved for the loss of who was then my best friend. It was that betrayal that hurt the most. The one upside of it such an ugly ending was that it allowed me to close things off because such betrayal killed any desire on my part to be romantically involved with him again (I'm fiercely loyal and it's a dealbreaker for me). My bf and I met only a few months or so after this break-up and although we didn't start dating for almost a year later, he saw the immediate fallout from it and how much work it took me to put myself back together. As a result, he despises my ex. So, this new offer of friendship did not sit well with him. Truthfully, I also was very skeptical---afraid that if I let my ex back into my life that he'd hurt me again---use me as an emotional crutch/filler and when he no longer needed that connection, he'd disappear again. 

After mulling it over for a while and discussing it with my bf, I decided to see if I could be friends with my ex again. I wanted to make sure he was okay with it. Well, I didn't think he'd be okay with it exactly, but I wanted to know if it was going to make him too upset. I didn't want to risk it negatively affecting our relationship or making him feel bad. Trying to be friends with my ex wasn't that important. My bf didn't like my desire to try to be friends with the ex, didn't really understand it (he's the type that doesn't have any desire to be friends with exes) and it made him uncomfortable, but he said that if it was something I thought I needed or wanted to do, he'd support me in it. I was hoping that the ex and I might be able to be friends again. I had missed my ex as a friend and always felt we were better friends than lovers. That's one of the reasons I was so pissed about how he ended our relationship. If it had been honorable, we could have been friends very easily and I wouldn't have been so crushed. He has apologized profusely for being so cowardly and selfish in how he ended our relationship and said it's one of, if not the biggest, regret of his life because it ruined our friendship as well.

So I cautiously attempted to be friends with the ex. It went rather well. I was pleasantly surprised, and I thought this friendship thing may work out. In 4 months, we've hung out only a handful of times and emailed or spoken on the phone a few times (so probably a point of contact every 2-3 weeks)--partly due to just life/scheduling issues, but also because I've wanted to move very cautiously, really give myself time to digest my emotions and not just fall back into trusting him so easily. 

I'm one of those people that can too easily forget the hurts I've suffered and remember the good times, which is great for not being bitter about crappy things that have happened but can result in having to learn the same lesson more than once. I'm aware of this tendency to, as my bf puts it, "find the soft side of a Grizzly bear"; so I try to move cautiously in such situations and make sure my eyes are wide open. I know it's sort of weird, but the ex is like a really good girlfriend more than anything---we kvetch and vent like two gfs about work, our families, relationship woes, etc. (I don't share relationship stuff with him about my relationship because I don't think my bf would care for that though he asks me advice on his dating dilemmas). He's really in touch with his emotional side (especially for a guy) and that is something that I really like about him and miss in my life as my other really good friends that are like that no longer live in the same state (my family provides almost no emotional support---they're very Irish Catholic and we were never raised with much emotional awareness---I'm the black sheep for this reason as somehow I got the reflective, introspective, emotional gene). I love to have those deep, soul-searching conversations that go on for hours and I've found that to be rare. I've found most folks just don't think like that or don't care to explore things in such depth or for such extended periods of time. It was something the ex and I shared and I think was the basis of our friendship, and probably what I miss the most about our friendship. I'm the type that has a small circle of very close friends---more like family---but since our early 20s, we're all over the US now so it's not like you can go grab a beer or see a chick flick with your best bud. My ex is the only exception to that as we both still live in the same city. If either of my best friends lived nearby, the idea of trying to be friends with my ex probably wouldn't appeal so much.

So, I've been surprised how non-dramatic this attempted friendship thing has been, both generally and for me emotionally. And so far, the ex has lived up to everything he has promised. He's been very respectful of my current relationship, been very adamant about not wanting to cause any strife with my bf and offering to do whatever the bf wanted to feel more comfortable with us being in contact again---whether that's meet him, only hang out if the bf is there, etc. I was hopeful that the bf may eventually be more comfortable with this situation and want to meet the ex (or when the ex finds a serious gf that we could all be couple friends). I know if the situation were reversed, that is what I'd want. Unfortunately for me, the bf has no desire to ever me et the ex or be his friend, even by association. And recently, he's told me that he's just really uncomfortable with the whole concept. This is my problem.

My bf hasn't been demanding, controlling or anything of the sort. He's just explained that it makes him very uncomfortable because he doesn't trust the ex, doesn't understand why he wants to be friends and also really despises the guy for how much he hurt me (and I think may feel a little inadequate---like what can the ex give me, even only as a friend, that he can't). So there are definitely some protective feelings as well as some insecurity and even a little jealousy (his words, not mine). My bf isn't the type that talks about such feelings easily, so I know this is a really big deal for him to have figured this out and to share it with me. I feel very grateful and honored that he could share such things with me so openly and non-defensively. I think it took him 4 months to tell me because he either didn't real ly know himself, was trying to see if the discomfort would dissipate and feels conflicted about it (is uncomfortable but wishes he wasn't). 

So I feel like I'm in this rock and a hard place situation. I'd like to be friends with my ex, but not at the expense of the discomfort of my bf. I told the bf that I'd cut things off with the ex out of respect for him as he's my concern and I don't want to cause him such discomfort. But that I was also very disappointed, especially since we started the whole friendship thing again (I wish he'd been able to say this when we first discussed the situation because then I would never have tried to reconnect with the ex as a friend). I kept thinking to myself if he only understood how important this was to me, he'd be able to deal with him discomfort--after all there are things about his life that cause me discomfort (he's a big pot smoker and drinker) but I chose to work through that discomfort and fear instead of asking him to cut bac k and think he could do the same for me. But then I flipped it and thought that perhaps it is me that needs to understand how important his side of things is to him--if I only understood how important it is to him, I'd never even ask for it. So that's why I decided to cut things off with the ex and assured the bf that if I felt any resentment towards him that I'd tell him and we could discuss it (he was afraid that I'd resent him for cutting off the friendship).

This may be just how it needs to be. Sometimes you can't get what you want. But I was wondering if you had any insights on how I could better understand the bf's feelings, or possibly help him better understand mine. Is there anything else I could do to reduce his discomfort (other than ending the friendship, which is how it currently stands)? I'm slightly hopeful that by just bending and proactively ending the friendship, that may be enough for him and a little ways down the line, he may feel more comfortabl e and say that I can explore that again. I also thought that the life circumstances that I mentioned in the beginning---especially the commitment discussion and the job/financial situations---may be contributing to his discomfort and when they resolve, that it may not be as big of an issue. Like he'll feel more secure in us as a couple so the threatening/jealousy aspects will be moot. 

I know this is a novel, Veronica. I really appreciate you taking the time to read it all. If you could offer any insight or additional perspective--or even just give me a "what in the hell are you thinking?" beatdown of a reality-check, I'd appreciate it. Perhaps I am way off here and I'm simply being unrealistic. I can't see the forest from the trees at the moment and am hoping that you can help me with that.

- Lindsey

Possibly the longest email I've received deserves a crazy long answer. Dear Lindsey,


Your boyfriend has every reason to be uncomfortable with your starting up a friendship with an ex that hurt you so badly. Every reason in the world. I'm completely on his side in this one. And I think you anticipated that. But let's go through it all.

It was amazingly generous of your boyfriend to tell you he'd support you in this, I'm sure hoping you'd figure it out on your own. However, you did work to form a friendship with the ex and the current boyfriend had to find the courage to admit to you his discomfort. I think you put him in a very difficult situation, and he handled it wonderfully.

It would be one thing if you and the ex had already repaired the friendship when you began dating your boyfriend. When you first enter into a dating relationship, there are ground rules. There are givens in the equation. Just like if you had a dog or if he smokes, you can't expect him to quit smoking just for you, and he can't expect you to give up your dog because he doesn't like dogs. It's not fair. It's the way you each came.

If he'd been introduced cerebrally to your ex as a friend in your life, that would be one thing. But that's not the introduction your boyfriend had. His entire frame of reference is that this 6 plus year former boyfriend of yours cheated on you and broke your heart. He only knows this guy as a liar, and an ass, and as any good boyfriend should he dislikes this guy for causing you such pain.

No matter what reasoning you want to put on it, there is something very odd about your wanting to be friends with the ex. Not enough time has passed and not enough "moving on" has occurred for either of you to innocently want to just be friends. The ulterior motives may not be horrid. Maybe he is so guilt ridden that this is a way to relieve it. Maybe you are that lonely for friends that you would actually consider him inner circle after what he did. And maybe the ulterior motives aren't so innocent. Maybe he wants you back, or wants to prove to himself that he can get you back on some level. Maybe you like the idea of the boyfriend being a little jealous, or maybe you like the idea that the ex realizes how badly he fucked up when he cheated on you and lost you. Whatever the deal is there, it's got agenda attached one way or the other.

I want you to seriously think about how you would be if this were the other way around. If your boyfriend had this major relationship before you with a woman that cheated on him and broke his heart, and left him wounded. And it took him a long time to heal. And you saw the pain and the damage she caused his gentle heart, the heart you now love. And then one day he says to you, "Hey the woman that destroyed me has returned and wants to be my friend. Cool, right?"

In all honesty what does your gut do? Do you smile and say, "Neato! Maybe I can meet her and we can all double date sometimes!" Be honest. That's not what your reaction would be at all, no matter how much you'd like to believe it would be. Your gut would knot and you'd say, "Why the hell do you want to be friends with her? And what the hell am I supposed to do with that!" And you'd be 100% right.

Time heals all wounds. Years from now when you are married and when the ex is married, maybe you two can have some kind of arms length friendship. But that time is not now. Especially not while you are trying to build a relationship with someone else.

When you are building trust with someone, you don't strain it and test it with obstacles it can't jump. There has to be some part of you that knew this was not gonna fly, yet you did it anyway. And now you're saying you've given in to the boyfriend's uncomfortableness because that's the correct thing to do, but you're feeling resentful about it.

I'm wondering if this was a set up. Did you create this so you could do some damage to this relationship as a defense mechanism to his not leaping to get married? To protect yourself from getting hurt? To pull away from taking chances especially in the aftermath of the family issues? To give in to the fear of financial ruin?

Or, was it a nice big fat combination of all of them?

The big tell here is that you gave a novel as you said of background. We all return to the fire. It may be subconscious but it's like a dog returning to its vomit. He doesn't know what happened, but even a dog can bring you to the place where it all went wrong. And say, here. Here it is, whatever it is.

You did the same thing in your email. You pointed out all the factors.

As self sabotaging as you may have been, you're also smart enough to call yourself out on it. You subconsciously pointed the way to all the answers, and then you sent them off to me, knowing I would give you a no-nonsense 3 martini kick in the butt answer.

At this point you really only have one thing you need to answer. Do you still have feelings for your ex. If you do, now is the time to be honest about it. If you don't, then apologize to your boyfriend for putting him through this stunt and don't look back.


Submit a Comment

  • JakeMcMurphy profile image


    8 years ago from Chicago

    I fully agree with your article. It really depends on the feelings that are still present between the ex-couple. If they both still have feelings for each other then they should be honest and open about it and explore the options. If only one has any feelings left then there should be space put between them so that there's no unrequited feelings (which are prolonged if there is constant contact).

  • profile image


    8 years ago

    manifest upon it and you shall receive it

  • Veronica profile imageAUTHOR


    8 years ago from NY


    Really the big thing you should do is to just be honest with the boyfriend. Let him take this journey with you. Tell him what you've talked about here, and that you're sorry, and whatever it is you're dealing with you would like him to help you and hold your hand while you find your way.

    You're right about the connections and the substitutes, and the Jung quote. Your current boyfriend sounds like a Zen trooper. As long as you give him the nods he deserves, I think you can handle the rest as it comes.


  • profile image


    8 years ago

    Thanks--Lisa and Timothy--other peoples' opinions really help.

    Thanks---Veronica (btw, I think you're pretty awesome too). What you said about denial really hit home. I know I have an issue with this---I have some sort of really strong desire to want to forgive people close to me that have hurt me really badly. I've been doing it with my family for years.

    I don't know if I'm trying to prove to myself that I'm strong enough--like I can take the hurt and still rise above it---or that if I can forgive and let them back into my life, that the hurt isn't that bad anymore, that I've healed it or moved past it in some way.

    There's this great quote by Carl Jung that comes to mind---"The greatest and most important problems of life are all fundamentally insoluble. They can never be solved but only outgrown." I guess in some way I want to prove to myself that I've outgrown the hurts---that I've moved pass them.

    And, truthfully, there is something incredibly comforting in the fact that he's acknowledged how badly he hurt me, regrets it terribly, wishes he'd never done it and asking for forgiveness---that there was some way to repair what he did because he deeply regrets the loss of our friendship. My family has never done this and I have no belief they ever will--I don't think they can even acknowledge the fact that they've hurt me so badly (it's easier to blame me for being too sensitive, too weak, too different than to see the real impact their actions have had). So maybe that's what I'm doing---acting out some of my issues with my family with the ex, and if those relationships can't be redeemed, maybe this one can.

    I'm sure there is some term in psychology for working out familial relationships through your personal, romantic ones (for example, why those abused by parents often seek out abusers as spouse).

    I'm not sure what to do about it, but I think denial as you mentioned is a big thing. I've got to find some way to come to terms with the reality of things, mourn them and let them go. I have no idea how to do that, but I'll work on it more.

    Namaste, Veronica. And thank you so very much.

  • Veronica profile imageAUTHOR


    8 years ago from NY

    Thanks Lisa, thanks Timothy~


  • profile image


    8 years ago

    This is really an incredible article. Thank you both for this. Lindsey thank you for the detail and articulation about everything. It provided so much that Veronica was able to give you a real answer and not just some fluff. Veronica thank you for the response. It doesn't just bark out an answer it leads the way. Like they say in math class, show your work! Well you did. This is really well written.

    Best of luck to you Lindsey.

    thank you Veronica.

    You have a new fan.

  • Lala_Lisa profile image


    8 years ago

    Awesome article Veronica and awesome comment. The point is made with her #1 too. He wanted to be friends with exs. It doesn't say they had cheated on him and hurt him and Lindsay only knew them in that way. So they aren't even comparable at all. The big thing with her bf now is that he only knew the ex as a cheater and liar and someone that hurt her so bad. Lindsay you can't compare the two. Your ex is up to something. that was very revealing about him what you said. He's no good. Great advice V!!!!



  • Veronica profile imageAUTHOR


    8 years ago from NY


    1 - your ex that wanted to be friends with his ex, cheated on you. That says a lot right there about that whole friends with the ex deal. The fact that one turned out to be a friend to you is beside the point.

    2 - You do realize you just compared your ex boyfriend to cancer, right?

    And lets go deeper. Cancer didn't look you in the eyes and say your loyalty means shit to me, I'm gonna go fuck another woman. Making something good out of something bad is very Kurt Vonnegut of you, and very empowering.

    Making something good out of the bad someone else did to you, is a very dangerous cycle of denial. It doesn't empower you, it helps you become a doormat.

    btw, I like you. I think you're pretty awesome.

  • profile image


    8 years ago

    Hey Veronica,

    Thanks so much for the answer. I can't say it surprises me, but I guess I just needed to hear it from someone not emotionally involved to really believe it--for it really to sink in.

    Just two quick things I wanted to respond to (one as clarification, one as something that occurred to me after reading your response).

    1)--I have been in this situation before, on the other side. My ex (the one I want to be friends with) was good friends with both of his exes before me (and still is). And my gut reaction was very much as you suggested (knotted, skeptical, a little threatened, a little jealous, a lot confused), but then I decided to meet them and had a very different feeling after meeting them. One, to this day, I don't care for. But the other, strangely enough, ended up becoming a pretty good friend. So although my relationship is over with him now, I'm actually still good friends with his ex. So I know it can be possible to be the new gf/bf and be friends (or at least friendly) with your bf/gf's ex. It's happened to me. That may just make me totally frickin' unusual, but it's what gave me some hope that something might be possible now that the shoe is on the other foot.

    2)--This is what occurred to me when reading your section about self-sabotage. That could very well be what I'm doing. I've considered it, but can't say with 100% certainty that's not what I'm doing. I feel much more connected within myself and hope to think I'm not being self-destructive like that, but I can't guarantee it. What occurs to me is that there is some sort of healing or redemption I'm seeking in a renewed friendship with the ex. I've found that in my life, my hardest personal challenges and greatest heartaches---one of the ways I healed was by using them to help others or to create some greater good from all the bad. For example, that's what I did after my Dad passed away (he had cancer). We cared for him until the day he died and all the caregiving was really hard. But after the deepest of the grief was worked through, I became a hospice volunteer. I knew exactly how it was to be in that position and helping others through it gave me great solace and it was a way I honored my father's passing and my family's and my grief in that loss--by helping others through theirs. I did the same thing after an attack in college. It became the catalyst of why I got involved in violence against women issues and groups. So, on some level, I guess I'm hoping that if a true friendship can be salvaged, it will somehow help redeem the bad break-up and honor some of the good parts of that past relationship. Perhaps a little too dramatic, but be some sort of phoenix rising from the ashes.

    I realize it's probably a foolish, vain hope. But I think that's what it is. I know I have no feelings for the ex on a romantic level. Even if our relationship didn't end badly, we would have broken up eventually anyway as we just ultimately wanted different things in life--who we were at 22 just wasn't who we were or wanted to be at 28/29. We were meant to be friends at best, not life partners. So I know it's not a romantic feelings for the ex issue---one of the few things I'm very certain of deep in my bones. I guess I just wish it could have been something else instead. This darn hope thing gets me all the time.

    Thanks for your candor and reality check; I really, really appreciate it.


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