Can You Fall In Love With One of Your Ex-Boyfriends?

I am a 43-year-old woman who has never been married (although I would like to be). Over the past 25 years, I have had a number of relationships while living in the U.S. and abroad. In the great majority of these relationships, it was the man who decided to break things off with me.

I am writing to seek your take on the phenomenon of being contacted by ex-boyfriends and girlfriends. In my opinion, once it’s over, it’s over, and I move on with my life. Yet I have been contacted by a number of ex-boyfriends (three in the past three years alone) telling me how they regret breaking up with me, how still love me and miss me, and how they wish they could have another chance. The most recent contact has been from a man whom I knew 14 years ago and who lives in another country.

I don’t understand what the point is of contacting someone from so long ago in your past, especially when you no longer even live in the same city or country. Are these men just desperate and lonely? Are they living in a fantasy world? These messages throw me into an emotional turmoil because, as I said, I would like to be in a serious relationship. When I hear from these men, I begin to remember our relationship and wonder if it would be possible to get together again. My job is flexible, and I can work from anywhere in the world. So when these men contact me, I do take it seriously. Any insight? –Almita

Anyone who claims not to be selfish probably doesn’t have a clear-eyed view of the world.

Dear Almita,

I never say never.

I may win the lottery. I may get divorced. I may get pancreatic cancer and be gone before I’m 50.

I think all of these things are exceedingly unlikely, but they’re possible.

So what do we know about men who broke up with you in the past and are coming back for more?

Well, without knowing either you or them as individuals, all I can do is prognosticate, based on what I know about people.

  1. People are selfish.They do what’s right for themselves first and tend to sort of hope that they’re not hurting you in the process. Anyone who claims not to be selfish probably doesn’t have a clear-eyed view of the world. It’s common sense to be selfish. To maximize your needs, wants and desires. It doesn’t mean you’re unethical. It just means you’re pursuing your own happiness.
  2. People are shortsighted. We act. We react. We make the decision that makes sense at the time. Sometimes it means marrying the wrong person because you’re 27 and “in love”. Sometimes it means bailing on the right person because you’re “not ready” to settle down.
  3. People grow up. I don’t know a single person my age who looks back 5 years and sees the same exact person. I knew a lot more at 30 than I did at 25. I knew a lot more at 35 than I did at 30. And, on the cusp of 40, I know a lot more than I did 5 years ago, when I was five months into dating my wife.
  4. People have regrets. Some folks regret things that they did – breaking up with an amazing woman. Leaving a comfortable job for a more exciting opportunity that didn’t pan out. Some folks regret things that they didn’t do. Try writing that novel. Asking out that girl. I try to live my life with no regrets, but even the best of us have moments of “what if?”

Despite the many heartening things I said above, which may sway you to think that you may want to give one of your exes a shot, I’m still skeptical.

Because even though people regret, change, and evolve, at the end of the day, there are some things that don’t change.

Character rarely changes. A cheater is usually going to be a cheater. A liar is usually going to be a liar. A poor communicator is usually going to be a poor communicator. It’s not that it’s impossible for people, through life experience and therapy, to improve on various facets of their life – it’s that it’s a pretty risky crapshoot to consider that the disappointing man in your past has suddenly morphed himself into someone consistent and trustworthy.

Of COURSE he’s going to say he changed. His intentions may be 100% pure. But that guy is still high-risk.


I know why it might be tempting to rekindle an old flame with the devil that you know, but I’d strongly lean towards the one you don’t know.

Because he’s already burned you, that’s why!

He dumped you. He hurt you. He went away.

And now that his life is not where he wants it to be… now that he’s feeling lonely and vulnerable… now that he’s going through his mid-life crisis and can’t seem to pull off hitting on 29-year-olds in bars…

Now he comes crawling back, begging for another chance.

Is he sincere? Probably.

Is he a good bet? Probably not.

He’s the same guy who dumped you before. He’s just a lot weaker and needier right now, because of his circumstances.

Listen, I know why it might be tempting to rekindle an old flame with the devil that you know, but I’d strongly lean towards the one you don’t know.

Decline contact with your exes, start with a clean slate, and trust that the right guy – the one who will be with you ‘til the day you die – is not going to dump you the way these other 3 men did.

Join our conversation (54 Comments).
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  1. 31

    I understand the temptation to attempt a second chance with an ex. Genuine connections AREN’T that easy to come by despite the billions of people on the planet. And if the break up took place within the last few years, there may still be feelings to build upon if the reason(s) for the breakup have been resolved.

    But after 14 years? That sounds like someone who is romanticizing the past because they aren’t finding anyone in the present. And the thing about romanticizing the past is, the person doing it tends to forget what the relationship was really like, and what all led to it’s ending.

    Almita, you say because you can work from anywhere in the world, when these ex’s contact you you take it seriously. You also stated in your opinion once it’s over, it’s over. So WHY are you taking ex’s contacting you out of the blue seriously? That’s what you need to figure out.

  2. 32

    @ Steve:

    How is it “lousy” to reject an apology, and a very self-serving one at that? That apology I got was full of excuses, no accountability. Sorry, but your judgment doesn’t work. I know what happened, I was there, I read the email. It smelled of just ego, and making HIMSELF feel better, NOT me.

    I don’t understand why people feel the need to come back, and apologise, years on down the road. I suspect it is ego stroking, trying to make themselves feel like a good person, etc. That is where I see ego playing in, in someone trying to get back together with an ex. Their ego many times is such that they don’t think about that other person. It seems like they don’t stop and think, “Hold on a minute. You know, they may still be hurting/don’t want to talk to me/have moved on and maybe married, so this might not be appropriate behavior.”

    I agree with the above poster about not allowing an ex to come back being about the good ego, it is a way of taking care of oneself, setting boundaries. I have had to set boundaries with myself, as well as with others, and kept contact with exes to a minimum. I do not want to give off any kind of vibe that I want to rekindle what we once had, and I also want to protect my heart from unnecessary drama.

    For me, this policy works because I have seen way too many people get hurt by going back to exes. Sure, there are exceptions. But for me, getting rejected once and then going back to it, is like being smacked, and then walking back and going hey, can you smack me again?

    “Fool me once, shame on you. Fool me twice, shame on me.”

  3. 33

    @P, @Mia: Agree wholeheartedly with what you said. I am from a country where arranged marriages are the norm and had an opinion that it is quite easy to pick a great companion/partner/spouse by going on dates frequently. This calculation drove the point home (and opened my eyes) that one needs to be quite fortunate even in the countries where dating is more prevalent to find a suitable or compatible partner. I find it both surprising and amazing that people break up for the reasons that Mia mentioned.

  4. 34

    Evan.. do you know you have a Russian name?:))
    It’s sooo right..

  5. 35

    I am finding this all very pertinent because only last week I took the decision to re-contact a guy I dated 2 years ago, when I saw his profile active on a dating site I’d just rejoined.
    The first time, we only went on 2 dates. I liked him, but decided to stop seeing him because he was very recently separated – I was quite shocked on our first date to discover he’d only been separated 6 WEEKS, and in fact hadn’t even moved out of the family home, yet. The thought of the upheaval he was about to go through (which he seemed blissfully unaware of !) made me nevous, and made me feel like I’d just turn out to be “rebound girl.” So on the basis of some minor infraction (asking to see me for our third date on a weeknight instead of a saturday) I called it off. I remember a the time thinking “this is the kind of guy you’d want to meet 2 years down the line, when he’s settled in his new apartment, his kids have adjusted to the new set-up, he’s been on a few dates – including a few bad ones – and has more idea of who he is now and what he wants.” So when I saw him on the dating site, I took a deep breath and recontacted him. I kinda figured it was me who’d called it off, so it was up to me (even though I’m the woman) to make the first move and make contact. We went out last saturday night. He’s been back in touch this week, but hasn’t set up our next date yet. To say I’m feeling wary would be an understatement – originally, I felt he seemed a bit clueless about dating, which was understandable as he’d only just started, but now 2 years on he still seems….well, a bit clueless. He’s keeping lines of communication open, but hasn’t arranged a second date. Is he already seeing someone? If so, why is he on the dating site every day, and why is he bothering to keep in touch with me? Its all questions at the moment, but if nothing else, I’ll lay this ghost to rest….watch this space!

  6. 36


    “So on the basis of some minor infraction (asking to see me for our third date on a weeknight instead of a saturday) I called it off.”

    I’m wondering why you didn’t tell him the truth? It’s perfectly reasonable not to want to date someone not divorced and not actually separated, if he hadn’t even moved out yet. Under those circumstances, I’d say he had no business trying to date anyway. When did the divorce become final? He may still not be ready, but best of luck.

  7. 37

    You are overthinking this. He is ‘clueless about dating’ because he did not set up a second date yet? Maybe he doesn’t know the set of rules of indirect communication you think men are supposed to know. Maybe he is asking out a few women right now. Maybe you are his favorite so far, but he has his kids this weekend, he is going on a trip, he had other dates booked weeks ago, or work is overloading him. Maybe you aren’t his favorite, he does not intend to go out with you again, but he likes to talk to you. Maybe he figures you are going to call it off again for a mysterious (to him) reason and so he is not investing an hopes in you at all.

    There could be loads of reasons you see what you are seeing, and you will drive yourself crazy trying to guess the reality and stalking him online.

    Reread the 5/17 blog. Enjoy talking to him. If he asks you out again have fun on that date and don’t worry about what it means. If he doesn’t, then you ask him out again, or let it drop.

    Ruby is right to ask why you didn’t tell him the truth. If I were him and learned that you used an excuse to break it off rather than being upfront even with yourself as to why, I would be wary of you.

  8. 38

    @ Ruby

    I think what I said to him at the time kind of incorporated both elements – when he suggested a third date on a tuesday evening (again!)2 weeks after our second date, (who wants to be “tuesday night” girl??!) I replied something like: “I think we’re coming at this from very different angles – I’m really looking for someone to BE with, whereas you seem too busy for that right now and seem to be looking for something more casual…” or something of that sort.
    As we’ve only met once so far this time around I haven’t grilled him about the details of his divorce, but he did spontaneously make a comment (in the context of “how’s life going for you?”) about how he was looking forward to his divorce coming through, so presumably its in the pipeline – in the UK a divorce where there are kids involved takes around 2 years, so it does sound as though he’s been pushing forward with that.
    Thanks for the good wishes – I have a sneaking feeling he’s still maybe only looking for “tuesday night girl” but I felt I had to give it a go.

  9. 39

    @ Helene

    What nights does he have his children? Maybe Tuesdays are one of his only regular free nights off. If you want someone available 7 nights a week or for spontaneous short planned trips or outings, you can’t date anyone with kids.

  10. 40

    I have also recently been contacted by ex-boyfriends. I am 38 and recently engaged to an AMAZING man who would likely have slipped through my fingers had I not read Evan’s book. The interesting facts about the two guys who have contacted me are that: 1) I dated both of them well over ten years ago, 2) they are both 38 years old, and 3) when I advised both of them that I am happily engaged to the man of my dreams, they quickly offered up lame excuses for ending the conversations and vanished. I was contacted by both of them within the past two months, and I have not heard from them since. One point that was quite interesting was that one man could not believe that I had moved on. Ego, it seems, can be debilitating for some.

  11. 41


    Your point about the kids is well-taken… I don’t have kids and in many ways am not especially keen on dating someone who does, however true to Evan’s teachings I am trying to be less rigid about my “list of requirements” in order to expand my dating pool and give people a chance. The reality is that I have found that in my age group (late 40s) among men on dating websites, almost every man either HAS kids or WANTS kids. The “want kids” guys I have to avoid as as my age I can’d deliver (no pun intended!) ansd if I rule out men with kids I’m ruling out practically everyone! Ideally, someone whos kids don’t live woth them would be easier… This guy has his kids living with himall week eveey other week, or something like that, so rather than seeing them on a set night a week he has a “week on/week off” kind of arrangement. If we do manage to get a relationship going I’m really not sure how I will feel in that set up but I do have a certain amount of anxiety about it – I suppose that my feeling is its up to him to make it work, by getting a sitter once or twice a week in the week he has the kids so that we can see each other -I don’t think I want a man who just “disappears” every other week. Obviously at the point we’re at we have not talked about any of this stuff so I don’t know what his viws are or how he forsees things working with a girlfriend – me or anyone else!

  12. 42

    Interesting discussion. I have worked with my ex part time since he broke up with me 3 years ago. Recently I learned that soon he may be leaving our work situation and I can finally have no contact. I have considered leaving our work situation as well, many times, and either way, one of us is likely to leave by the end of this year. While I very much look forward to no contact and being able to completely put him in the past (which is difficult to do with regular, sustained contact with an ex) I have a very strong intuition that he will contact me in the future and try to spend time with me. It will be “safer” for him to do this without having to work together.

    I know he is still single, and after reflection, it is obvious he left me because he felt he could “do better”. He wants a younger woman but I think perhaps he is getting his comeuppance – despite his good looks apparently it’s not that easy to find a woman 10-20 years younger as a partner. He is not broke but he is certainly not rich.

    After he broke up with me (twice) I was very depressed but I had to put on a facade in order to work with him. It was draining but somehow I came through on the other side. At this point it is perhaps possible I can be friends with him…although I am afraid that it could be tempting for both of us since neither one of us is seeing anyone. I plan to be strong and not give in to any overtures since history does tend to repeat itself and I really don’t think I need to be dumped a third time.

  13. 43

    well, for once I disagree, I am seeing an ex whom I have always loved and vice versa after 25 years of both of us having bad marriages. I was part of the issue being very immature and selfish and wanting to be married and finding out now that my dating during the relationship is what ended it in the first place even though I was open about it. But one-sided openness does not mean both parties agree. I also was rather narrow minded in my religious beliefs.

    So now we are getting to know each other all over again. He has become more considerate and communicative, I now know how to listen and have broader interests, much to his surprise. We both are in our 50s and hope to be together before we get too old, as I think we both feel this time it will have to be for keeps. But there are some exes that are a definite no, not now, not ever.

  14. 44

    Елена, Привет! The English spelling Evan is Welsh, which is an Irish way of putting it. It is from the same root as Ivan, Ewan, Jean, John, Sven, Sean, Shaun, Sion, Johannes etc.

    The new is always bright and shiny. I saw an article in the New Scientist which calculated that if you hadn’t found the perfect match by your 7th attempt then you should settle for number 7. In fact you should aim for 7, each one being an improvement. At 7 the chances fo further improvement are extremely small. (This applies to women. It takes years longer for the majority of men to reach #7 so men should settle at 5 if they get that far). If you have reached 7 then the men in the future are unlikely to be improvements on the ones in the past. You have the advantage of knowing how their strengths and weaknesses play to yours and you can negotiate processes for dealing with them in cold blood. If you have had less than 7 relationships (over 3 dates), try a few more. If you have had more be grateful for a chance to reduce uncertainty.

  15. 45
    A Lone Soul

    What about if the two of you had been extremely good friends many years ago –even evolving into “flirting friends”– but the timing was always off to connect in a deeper way?

    Whenever I found myself falling for my very special friend back then, I pushed those feelings away, because I was convinced that he only felt a loving friendship for me. It wasn’t until after I married someone else that he did some soul-searching and realized that he really loved me. After he told me, I was shocked and had to do my own soul-searching. After finally putting all the clues together, I saw the depth of my feelings for him as well. But of course, by then I was deeply committed to my marriage (despite discovering major character flaws in my husband’s personality), had just purchased a first home (with a huge mortgage), and found myself unexpectedly pregnant (years ahead of plan). Feeling overwhelmed and vulnerable at the time, I let my “friend” slip away.

    I have endured many, many years filled with regret –for being so young, stupid, and clueless! “If only I had….”; “If only he had….” But we didn’t. If he were free now, I imagined that we might actually have a good chance to really connect. We each suffered the pain of loss without actually having had the full-blown love relationship. But it isn’t quite the same as a “failed relationship.” I have no interest in reuniting with any true past boyfriends, but it’s precisely because my “friend” and I were never a couple that I long so intensely for a second chance with him.

    Does this kind of situation resonate with anyone else?

  16. 46

    So cynical…I dumped a good man 25 years ago for the wrong reasons but at the time I felt for him they where right.  He was 7 years younger then me, I met him and my eventual long term partner just after my husband had left me and my 2 very young children.  I loved this young man but he was so young, only 19,
    his parents wanted more for him so I walked away and settled with the other man who was my age and a little wiser but maybe the poorest choice I made. 25 years later through a friend the beautiful young man I knew is back in my life, older, wiser, more confident and we take each day as it comes but whatever happens I know he will always be my friend, oddly the ex husband and I are now the best of friends as with the other men I have dated.  The one person I am not in contact with is the person who I settled with, the man who I thought reliable but turned out to be a controller and a wife beater!

  17. 47

    My husband of 33 years walked out on me on September 16th, 2013, and I was in a total state of shock and hurt from it all. Then, only 4 months later from that trauma, I received a phone call from my brother, David in NY, telling me he had just found my ADOPTION documents hidden away in our father’s apartment-and neither of us ever knew this, and I cried for another 5 months about that hurt and pain.
    Then one night, feeling very alone, and going to bed early, I woke up and logged onto my Facebok page, and “low and behold”–was a message from an old college boyfriend that I had dated way back in 1977, before I joined the U.S. Navy in 1979, He gave me his cell phone number in the message to me, and I called him up. We have reconnected with each other again, but he lives in Charleston, SC and I live in Bellingham, WA-clear across the country from one another.
    We spend hours and hours on the phone with each other, and he tells me he regrets not marrying me, and taking me away from my abusive mother. He regrets not finding me sooner, but I tell him it wouldn’t have gone well if he did find me while I was in love and married to my husband. so things do happen for reasons.
    My only question now would be “Do I allow this old boyfriend to continue to pull at my heart strings? Do I want him to be the one to fly out and see me, and maybe we can establish something more permanent? I don’t want to ever be the one to chase him, because I don’t want to get hurt again, like I my husband severely hurting me when he left me.
    I want to date again, and am ready to just start going out again, and feel that my old boyfriend and I have great history, commonality, and things in common, and know he won’t hurt me, like if I started with someone new. But, again, I am taking it cautiously now.

    1. 47.1
      getting older

      meet half way…?  go on a holiday together and just see how it goes on neutral ground.  don’t play the who goes to whom game as it’s not the 50s any more.  women are independent and want equality… also being cautious is okay but no pain no gain.  you can’t get close if you don’t want to take a chance… but it’s up to you whether you are ready to let someone into your life and heart again, … still being pen pals hardly equates to a ‘relationship’ does it?  Do you want to live a life of passion or just stay on the banks of the river watching life go by?  It’s entirely up to you.  River banks are nice places to be.

      I’m divorced, though I think of myself as single because it was so long ago.  I am not adopted but there is a positive side to both these experiences in your life.  One of those is simply how much compassion and understanding you now have.  You sound like someone who had the rug pulled out from under you.  I know what that is like.  I spent four years of my life without any family support raising two young kids as a single mother on a low income.  It felt very shaky for a long time and I spent a lot of time feeling like a victim in one way or another.  Then I moved on to become an agent making plans to have the life I choose or make for myself, not a life of what happens to me.

      Now I’m trying to learn gratitude and I’m not always good at it/ I forget myself and start focusing on what has been lost rather than what is and what could be.

      For example being adopted I guess you often think of the parents who chose you rather than those who gave you up (or from whom you were taken)?  I imagine it must feel great that someone wanted you and chose you.  There are plenty of kids who were raised by the parents who accidentally brought them into this world.  It’s easy to romanticize about other people’s family.  I was raised by my biological parents.  My father never sees me now, even though we are quite similar and find it easy to connect.  Recently he went through a very convoluted path to try and contact my adult kids rather than just go through me.  My mother is loyal and supportive in a practical way as much as she is able to be, but just isn’t able to connect with me on an intellectual level, or emotional level.  Thus I feel quite alone in the world and need to tune in to everything I can be grateful for eg. my daughter being a big part of my life.  The way I see it most family arrangements are far from perfect, united, close and happy.  I also observe many marriages are far from ideal.  Comparatively, or statistically it’s not more negative being single.  Maybe it’s all about your state of mind so by all means give yourself all the time you need.  That’s my thoughts.

  18. 48
    Jay Johnson

    Been there myself. I have wondered the age old question…


    If you could go back into the past for second try would you? But no time machine and looking at reality now after a decade or more you both have changed considerably and are not even the same people. Your two lifestyles have taken different paths. It would be a very difficult attempt to say the least. I know in my past I have had less than a handful of girls who burned me very very bad. I found the best way to get over them was to spend all six weeks if spring break on the east coast beaches of Florida. Hot beautiful blond girls all over those beaches looking for a great time!

    At one point they wanted back after a year or so and I always said NO. While I may have considered to try with them again, and even today decades later I still have highly detailed memories of being hurt, I still said NO just after a year or so. For one thing knowing they have been with many other guys after dumping me then they want back rang a bell that those other guys did not want them for some reason. And at that time there was and there still is over a billion age appropriate females in the world with half of them single and available at any given time. You know the saying, there is plenty of other fish in the ocean.

    I would say be very very careful. Once in a while it works out for the best but those are very very very rare. Best of luck.

  19. 49
    getting older

    How about letting them come to you and just cautiously spend a bit of time getting to know them again?  I agree with P, there are not millions of people with whom you can connect intimately later in life.  You are still young enough to be attracting new people, but, you know nothing about them so it’s starting all over again each time.   The older you get the more of a past people have.  How much are you willing to invest in having a relationship?  How busy are you with your career or work and other aspects of life?  One thing I’ve noticed is not having the same level of energy to invest in social situations.  There’s nothing wrong with re-uniting when it comes to old/long lost friends, so why make a distinction with lovers/bf/gfs?  It really depends on the individual and on what still remains between you.  Also, I’m sure with the level of life experience you now have, you are better at judging each circumstance as it happens.  You know your limits and boundaries now, but maybe you also know you can’t get anything for nothing.

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