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

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.

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  1. 1

    Almita, sadly Evan is right. Try to find a way to ignore these types of overtures. If nothing else, they showed that they had poor judgement when they broke up with a terrific woman like you, right? Regardless of what happened when, at the end of the day you deserve to be in a loving relationship with a man you don’t already know is willing to dump you.

  2. 2
    Flower White

    Don’t do it. Don’t go back. Evan is right.

    The last guy I loved was two years ago and I’ve been single ever since -he and I broke up in couples therapy. I gave the breakup a ‘soft landing’ with help of the counselor. Why? At first he was charming but he proved to be short tempered and overdrank. No can do.

    With negotiation from the therapist I went over his house to pick up the last of my items (we didn’t live together), but he started to yell…then picked up the phone to call the police to have me escorted off the property “my ex is here causing a scene, come quick!!” I did nothing to provoke him. He was hurt and lashing out.

    How humiliating that he would stop so low to lie to the police! Of course I left immediatly and swore never to be alone with him again as he proved himself untrustworthy and dangerous.

    Took me some time to get over that.

    Guess who came back a year later asking for another chance? Emailing and phoning. Asking me to dinner. Asking for forgiveness. Saying it was hard out there. Saying that I was one of a kind, one in a billion, etc. etc. Begging for forgiveness, one more chance.

    After blocking him in every possible way he somehow found my new phone number so I told him to stop or I’d file a restraining order.

    He showed his crazy side again, for the final time- called me all sorts of names and said have a nice life. Haven’t heard from him since.

    Imagine if I had gone back and given him one more chance to bring the crazy!? Billions of men in the world. Never look back!

  3. 3
    old lady

    I am going to disagree on this one. Yes, people change with time but deep down are probably the same person. I feel the woman should think back on the individual relationships she had with each man. What was the reason for the break ups? When thinking back on the relationships, were they too young, refusal to convert to his religion, differing views on marriage, differing goals toward life and family? A man will leave if the female is unable or unwilling to meet his criteria at that time for marriage. If with any of these men, circumstances have now changed with the passing years then giving it another try may be worth her time. If this woman feels that upon looking back there was a past mate who at the time she could not meet his criteria for a relationship and marriage but now can. If I were this woman I would reply to that man and give it a try with eyes wide open.

  4. 4
    Karl R

    Almita asked:
    “When I hear from these men, I begin to remember our relationship and wonder if it would be possible to get together again.”

    In my breakups, I’ve always considered that the person who broke things off is the only one with a reasonable chance of rekindling things.

    However, it takes more than a change of heart. To quote a book title: “It’s called a breakup because it’s broken.” In order for there to be a chance going forward, you have to determine why it was broken, and whether the underlying problem has been fixed (or will be fixed).

    To give you an example where things could work out:
    Several years ago I dated a divorcee who had two young children. We broke up because she wanted to pursue a relationship with someone else. I had also been reluctant to get too serious because she had joint custody of two children (and I didn’t want kids).

    Let’s suppose the two of us were simultaneously available 15+ years in the future. She has already dated that other man, and they have split up. And by that time, her kids will be grown and gone. The two main issues will have already resolved themselves, leaving a reasonable chance moving forward.

    But there are some other situations which make my (hypothetical) situation easier than yours. We live in the same area and still cross paths in the same social circles. Dating wouldn’t involve a long-distance relationship or a move. My hypothetical situation requires less investment than yours and is probably more likely to succeed.

    Almita asked:
    “Are these men just desperate and lonely?”

    They’d like to be in a relationship, possibly a long-term one. It’s easy to forget the problems and remember the good parts of an old relationship. But I don’t see any indication that they’re more desperate and lonely than you. (But they’re probably less cautious, which should encourage you to be more cautious.)

    Almita asked:
    “Are they living in a fantasy world?”

    Not really. They just took an action (contacting you) which took minimal investment, and has a chance of being successful in the long run. Dating (from the man’s perspective) is filled with low investment / low return actions.

    Even in my hypothetical situation (where the major problems are clearly resolved), I wouldn’t pursue an inconvenient relationship. I’d limit my dating to women who are in the same city.

  5. 5

    I disagree with the idea that people’s characters rarely change. In fact, one argument against re-connecting with the guy from 14 years ago is that you both have probably changed a lot. And odds are not in similar directions.

    I also don’t equate selfishness with gaining happiness in this world. In fact, I’d say that the ability to over-ride much of our selfishness is a key to any healthy relationship.

    Furthermore, people successfully reunite much more often than winning the lottery. Personal situations change. Priorities change. Level of relationship wisdom changes.

    With all of that said, I’m still inclined to agree with Evan’s general skepticism. Pleas asking to get back together again coming out of the blue smack of desperation. Instead of making the effort to strike up a conversation and learn about where the other person is at, and whether there even is attraction and interest present, what’s offered is a bunch of assumptions. Which indicates pretty unclear thinking, as well as a lack of respect for the fact that X number of years have passed, and you have moved on with your life.

    In other words, how someone contacts you tells you a lot about where they are at. If someone sounds desperate, they probably are.

    “These messages throw me into an emotional turmoil because, as I said, I would like to be in a serious relationship. ” This is where you, Almita, need to examine things more closely. Is any of the turmoil coming from truly wanting to meet someone again and see if it could work out? Or is it just your own loneliness and disappointment over not having that committed person in your life? If you haven’t thought much, or at all, about these men over the years, then I’d guess it’s the latter.

  6. 6

    I agree with a poster that you should judge each on a case-by-case basis. What was the relationship like, why did he (or you) quit the relationship, how long had the relationship been, how close had you become, what was the guy even like, if he left you for a particular reason then has that reason changed, etc.

    In my experience, guys from your past are from your past (and not your present) for a reason. Since I’ve been divorced, I’ve had a number of men from my past reach out to me. Each time I’ve met them, or befriended them, or even dated them, I’ve soon realized why they were in my past & not my present. I wondered if I had made a mistake in marrying the guy I’d divorced and if I should have dated those guys instead. Each time I realized that, no, I made the right decision about all those other men, even if I was just in high school, college, or a young adult at the time. It let me know that, even back then, my judgement was sound & reliable.

    Finally, if the man is serious about approaching you, then he should be willing to put his money and his feet where his mouth is. He should be willing to fly to where you are and court you. Just because your job is flexible does not mean you should do the heavy lifting. Because he’s the one asking you for something, he should show that he is serious in his ask.

  7. 7

    Nathan @#5 said: “In other words, how someone contacts you tells you a lot about where they are at. If someone sounds desperate, they probably are.”

    Exactly! And I would add: how someone breaks up with you also tells a lot about who they are.

    Dumping you and then showing up in your email inbox out of the blue months or years later with no idea of where you are at to request a second chance is incredibly self-absorbed and not a good sign of improved character and relationship skills. They do not even know who you are at that point, and if this is not desperation, then I do not know what that is.

    I agree with Karl @#4 that in some instances, reasons to end a relationship become irrelevant years later, therefore it would be a whole different story to meet up again – after a previous compassionate ending of a relationship – in a common social circle and realize that circumstances have indeed changed.

    As Evan always says: “People to do what they want to do”. From that observation, we can look at things rationally and make wise choices for ourselves.

    I’ve also experienced the “returning of the ex phenomenon”. As Karl said: low investment, low risk for them! Actually each of them came back months or years later, regardless of who had ended up things. I would quickly remember the lack of compassion in the “disappearance act” if he had disappeared, the lack of self-esteem if I had ended things, the incompatibilities I had overlooked, and the narcissism of the “coming back” out of the blue assuming that I was waiting for them, holding my breath. That speaks volumes of their character. So that was relatively easy to ignore, say NEXT! (most of them time I was indeed dating someone else), and a couple of years later meet my out-of-this-world boyfriend with whom there is no previous disppointment, no history of disrespect and narcissism.

    It’s tempting to give in in the ease of microwaving left-overs, but fresh is always better, and well worth the patience and the work involved.

    1. 7.1

      although your arguement sounds nice its flawed as time is your biggest opponent. While your out there single trying to find love you’re competing against others that are more genetically gifted and maybe more financially sound. when you start to think of starting fresh it’s hard to fathom when you yourself maynot be fresh because as humans we age. When it comes to finding romance no one wants to date an older person who has flaws and misplaced expectations. Maybe an ex can be a renewed contiuation but in other cases starting fresh means relying on someone who may not be the best person but the only person available. dating is a numbers game and people die thus lowering and increasing the dating pool. I hope your someone who can keep a fresh outlook on life and maintain an excellent level of health otherwise you may find yourself relunctingly calling upon your exes..

  8. 8

    This really depends on why the breakups occurred. However, I have also been contacted by ex-boyfriends who regretted breaking up with me, and in one case, I contacted someone whom I had broken up with. Each one swore that he was a changed man, and I think a couple of them did actually love me. But the problem was that none of them had actually changed, so the same issues just re-occurred.

    After so many disappointments, I finally decided to put all my exes in the past for good. Although I always want to leave things on good terms, I made a decision not to remain active friends (Passive Facebook “friends” is the extent of any contact). I wanted to clear away any negative energy or roadblocks from my past. I’ve also tried to forgive the guys I’ve carried any anger towards, to realize that I am not a slave to past mistakes, and that I’m better off without them. Lo and behold, a few months ago I met a wonderful new man who treats me better than any of them ever did. I now see with utter certainty, that these men are my exes for a reason. No matter how old you are – and I’m middle-aged – a good relationship is worth waiting for.

  9. 9

    Also, it’s not even so much that the men didn’t change, but the way that the two of us interacted together had not changed.

  10. 10

    If they’re cheating on their girlfriends, NO!
    But if they’re single and were too young the first time around….
    Also, you are in turmoil from one contact. That leads me to believe no relationship will work because you are not stable.

  11. 11

    I recently made a similar decision to Ruby around some exes or former love interests from my past who I realized never would be real friends, nor should be considered potential dating options. I even cleared them off of Facebook because it seemed like completely cutting them out made the most sense. I have a few other exes that have become valued friends, which is one reason why I think closing the door on all exes is excessive. But I do think that if you reflect back on a relationship and remember a lot of difficulties and misery, it’s best to stay looking forward, and to leave that person in the past.

  12. 12

    I think it has to be case by case. I ran into an ex who I dated for 3 yrs, at a rest stop on the highway half way across the state, were mid-20’s, broke up to differences in what we wanted, we got along but I wanted to get more serious he didn’t. Haven’t seen him since. At the rest stop we made small talk, told him I was newly divorced, we exchanged contact info (He is exiting a miserable marriage of his own). We have had JUST LUNCH every month or so since last summer. We live and work 45 minutes apart so its not convenient. I have no idea if anything romantic will evolve, he knows I date on-line and otherwise, he is still wrapping up a divorce, nobody wants to be a rebound. However, we both find comfort talking with each other, and actually getting to know each other again. We have evolved into different people over 24 years, but in many ways we are still the same, familiar. Maybe Karma had something to do with us bumping into each other at such an odd location at that precise moment. The door was closed 24 years ago, but I am glad to have rekindled a friendship.

  13. 13

    If you are up for another dose of emotional pain & disappointment, just get back with an ex. Evan is right on this one. There are literally billions of people in this world that we have not met yet. Shut the door on the past & go out & open some new ones.

  14. 14

    Like Evan says..never say never. However…my belief is that when a relationship ends, there’s a good reason it ended, even if that reason isn’t immediately apparent to the one who was left. I always thought if a man left me and came back later, it was a sign that “it was meant to be,” that he’d come to his senses and realized what a good thing he let slip through his fingers. Nah. The cold reality is that he’d simply hit a dry spell and was yearning for the old familiar. Fast-track style, as if we could dive right in right where we left off, no need for reflection or a slow pace to get reacquainted. Nothing good has ever come from me allowing a past lover to re-enter my life. And if he left me once, it’ll be even easier for him this time. I don’t owe a former lover a second opportunity to leave me. And if it was me who ended the original relationship, I trust my instincts were right the first time around.

  15. 15

    I think it very much depends on the person, and why the relationship ended. There are some exes whom I am more than happy to leave in the past, and if they were to come knocking on my door again, I would feel quite comfortable declining, because we were simply not compatible.

    However, I think that sometimes relationships break up because one or both of you lacked valuable relationship skills, and these can be learned and are more likely to come with maturity.

    I think you should treat an ex (that you are willing to give a second shot) like any other stranger you would start to date and take time to get reacquainted, and avoid rushing in and getting too invested too soon just because you know them.

  16. 16
    Speed Dating Liverpool

    Yes, peple make mistakes, people regret, people come back, people change. But you cannot swim in the same water twice, so if this person disappointed you at once – that wiil probably happen again.

  17. 17

    I am a big fan of the saying, “Exes are an EXample of what not to do in the future, in a relationship.”

    I do not accept guys coming back for a second chance, nor even an apology. Two years ago, a man I dated in college who was physically abusive to me, found me on Facebook and sent me a private message to apologise for the abuse, from seventeen years ago. I replied with: “X, the time for you to apologise to me was seventeen years ago, not now. There is never an excuse, never a reason to hit a woman. Ever. Do not contact me ever again. I don’t want your apology, nor do I accept it. Abuse is unforgivable in my book. Stay away from me.”

    I don’t need, nor want, a second chance to get rejected all over again, I’d rather start with a nice clean slate, than get involved with someone who’s already hurt me before. Thanks, but no thanks.

  18. 18

    I’m going to disagree with the idea that outright rejection of the idea of rekindling something with an ex is the rule, and agree with some of the people who have so far said it depends on the circumstances. I think the concept depends on several factors.

    First, if someone was abusive (in any fashion) or there were simply unpleasant realities to the original relationship, then yes…outright dismissal of the idea should be the rule.

    However, a good number of relationships don’t break up because of this reason. Often times (and nobody likes to come out and say this, but it does happen quite a bit) one person decides to exit the relationship because, in one way or another, they think they can find something “better.” Should this be a point of automatic dismissal? I’m not so sure. Often times this point of view comes about because of immaturity (at the time of the original relationship). This is usually what is meant when someone says they are not ready to “settle down”–they believe something better is out there. Now, whether or not this should be taken as an insult really depends on what kind of expectations this person had–and quite a few people have really lofty expectations and immature views of this.

    In cases like that, depending on the time passed, sometimes I think its a good idea to take a look at it again. Was the relationship generally a good one? Did it end on amicable terms with dignity and honesty? I’m not talking about the reaction of the person being broken up with necessarily, but how the person breaking it off accomplished the task. If the general answer to these was “yes”, then perhaps there’s a chance.

    (Before someone says that its a bad idea because they thought they could find someone “better” and going back with them would be “settling”…I want to point out that obviously they determined they were wrong, if this is the case. Your ego doesn’t apply here unless you choose to look at it that way)

    If there is a chance, its also going to depend on YOU. Are you someone who holds grudges and are therefore going to look for things to be wrong? If you are, then its not a good idea.

    To those that say there are “plenty of fish” out there, and in one case above “billions of people”…I’d like to point out a caution in this belief. I grant that the internet and world globalization have “expanded” the dating scene quite a bit…but a little bit of rational thought about this is a good idea. If this was someone you had a connection with, that’s NOT a common thing and should not be taken lightly. Let’s use some numbers here to put aside this rather obnoxious belief:

    First, you could potentially go out on a date per night (yes, some could do more, but let’s be more realistic). That’s attempting to superficially connect with 365 people per year. Assuming an average dating range of 30 years (yes, we could adjust that a bit, but I’m using an average: If you are 20 and looking to settle down and get married with kids, its roughly 15-20 years for women realistically and even that is stretching it)…wow, that’s 10,950 potentials. Not billions by any stretch…but…not terribly shabby.

    However…in order to really determine if you have the makings for a relationship here…this is not generally what happens. Most people go out on a date or two per week (hey, we do have other things to do), so now we’re down to yet a smaller number: 1560 to 3120. That’s assuming you “rule out” the relationship on the first date, which sometimes happens. HOWEVER, let’s assume you spend more than one date with this person, with an average of “getting to know someone” over the course of 2-4 weeks before some are ruled out. Factoring that in with the original 1-2 per week (the math gets complicated and I won’t bore everyone with it) and now you’re ACTUALLY down to under 1000 in that 30 years. NOW, let’s factor in an average of 5-10 relationships you have which go several months to a couple of years in that mess (and assuming said relationships don’t work out). Ugh…now you’re down to, REALISTICALLY, a pool of PERHAPS 100-300 if you’re lucky. Perhaps if you are really prolific in the dating scene you could up your numbers a bit but that would likely be a losing game as you would not likely really be getting to know anyone very well.

    Now here’s the additional kicker–of that pool (at any stage above), you also have to consider that THEY may not continue with or be into YOU. Yes, its the old “its not all about you” thing. So, roughly cut those numbers in half (as an average) as they all assume everyone in that “list” is agreeable to YOU as a potential.

    What this all means is that I don’t believe its necessarily a great idea to completely rule out anyone you may have had a connection with, provided there weren’t overt issues in the relationship itself. You DON’T have “billions” of other choices or chances at a connection with said many people. You simply don’t, as much as you might like to believe you do. Don’t take a connection with anyone lightly.

    1. 18.1
      getting older

      agreed…. i think statistics have a useful place…. the older we get the less often we “connect’… whatever that means

  19. 19


    So let me ask you something. Would YOU want someone back in your life, who left because they thought they could “do better”?

    No thanks. Sure, maybe a relationship ended on good terms, maybe the other person didn’t know that the dumper was looking for something else, and realized that they were wrong. But really? Do you really want to chance that one more time?

    I used to date exes, years ago, and even dated a former boyfriend, shortly after my ex husband and I were legally separated. I realized very quickly why this former boyfriend, was a FORMER BOYFRIEND. Stood me up for dates, did not call like he said he would, etc. People rarely change their character, despite what they’ll tell you.

    It’s like EMK has said, time and time again. Believe it when someone shows you who they are. My exes showed me who they were as people. Sure, my ex fiance did grow up, he’s married now, in another state, and happy. But if something happened in his marriage, and he contacted me and wanted to try again? I’d say absolutely not. I’d been there and done that with him, and while he’s not a bad person, there was no abuse or anything like that in the relationship, I’m not sure I want to find out again what it would be like if he left. No thanks.

    I have been “too nice” and too forgiving to men who did not deserve it, and I am no longer that sweet little doormat I was in my 20s. I am older, wiser, and not about to put up with anyone’s games or commitment issues. Guys get one chance with me. One. They blow it, they are gone. I am too old for the drama.

  20. 20

    Uh…Evan may say it, but he’s quoting Maya Angelou when he writes: “When someone shows you who they are believe them the first time.”

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