Should I Judge Him For His Last Relationship?

a couple on white bed staring at each other

Hi Evan,

I’ve been a long time fan of your blog and appreciate the advice you give. I’ve been dating my boyfriend for six months and love him very much. In many ways, he’s everything I’ve been looking for.

Recently I found out that there was a significant age gap between his ex-wife and himself. It’s not so much the age difference that I have issue with — the issue is that she was only 18 when they met and he was 34! (They married when she was 23 and she cheated on him two years later.) I know I should not judge a person for his past, but I’m having trouble getting over this issue. I’ve lost a bit of respect for him. It makes me question his judgment. Maybe he’s not the person I think he is?

I’m worried that if I can’t move past this and concentrate on the present that it will doom our relationship. Thanks. —Ava

Oh, Ava,

Let’s just imagine what it would look like if men judged my smart, strong, successful clients for their previous relationship.

Let’s just imagine what it would look like if men judged my smart, strong, successful clients for their previous relationship.

You’d discover the woman who spent eight years “dating” a man who NEVER agreed to be her boyfriend.

You’d discover the woman who spent 20 years with a husband who was verbally abusive.

You’d discover the woman who’d never had a relationship longer than 3 months.

You’d discover the woman who fell in love with her fuck buddy and pretty much consented to an open relationship for a full year.

We can go on, of course, but it’s very poor reasoning to hold someone’s past against him.

For ten years, I dated online prolifically. I hooked up a bunch, and a handful of exclusive relationships, ranging from one month to eight months, but what would that tell you about me? You might think I was a player or a user; in fact, I was desperately looking for love.

I broke up with the women who I didn’t “feel it” for in the first three months.

And all the women with whom I was most enamored dumped me.

In other words, I acted with integrity for the majority of my prolific dating career.

Still, at any point in time, you could have convicted me for having a girlfriend who sent me anonymous hate mail after our break up, or having a girlfriend who tried to assault her roommate with a pewter candlestick. But it would be a short-sighted mistake, reflective of a time that I was a) too young, b) overly reliant on lust and c) particularly lonely.

If your boyfriend is a chronically bad decision-maker, what does it say that he’s chosen you as his girlfriend?

Finally, as much as I would never be the 34-year-old who chose an 18-year-old — especially since I’ve always liked older women — there are always exceptions to every rule. We know a couple who had a similar age difference — he was 35 and divorced and she was 20 or something like that. Fifteen years later, they’re still happily married.

So, Ava, is your boyfriend a chronically bad decision-maker? Or did he just make a stupid mistake based on passion, like everybody else on the planet?

I’m guessing it’s the second one. And if it’s the first and your boyfriend is a chronically bad decision-maker, what does it say that he’s chosen you as his girlfriend?

Sorry. That was too easy. But to sum it up from the best book I’ve never read: judge not lest ye be judged. I don’t know what you’ve done in your past, but if you’re single, it’s probably pretty embarrassing like the rest of us.

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  1. 1

    Thank you Evan!!   What a great reminder.   Just last night my sister was telling me about a guy that she has seen a couple of times and she has a judgement (and so did I) because of what he told her about his last relationship.
    I don’t want to be judged on my past relationships.   If a man were to look at my past he could easily conclude that I am not good relationship material.   I called my sister, read what you wrote and we discussed it.   We both agreed that we did not want to be judged for our past.   She reminded me that not only do we need to not judge others for their past we need to quit judging and forgive ourselves for our past choices.

  2. 2

    I don’t know.   When it comes to exes, I think it’s more admirable for people to take ownership of their past.
    I’ve asked follow up questions about my exes’ exes.   I don’t take too much stock or judge them for having failed relationships. Points for honesty with Ava’s guy, but there’s still an elephant in the room…
    A 34-year-old is thisclose to committing statutory rape by getting involved with an 18-year-old.   And the reason the relationship ended was not he realized a maturity gap.   If I were Ava, I wouldn’t judge him for it, but I would be curious if he was emotionally immature/stunted and how he ended up dating a teenager in the first place and if he’s a creep.
    The easiest thing to do is just ask.   Say “Eighteen year olds are REALLY young.   What brought you together and attracted you to her in the first place?”
    If he says, “She was really mature,” I’d think twice about whether or not he was mature. (If he gets defensive, he is definitely immature).   No 18-year-olds are mature, and the fact she cheated on her husband shows this.
    “She was vibrant, fun, I loved her energy but looking back, we were definitely from two different worlds and I thought she was more mature than she really was” yeah.   “I was a late bloomer and was more comfortable around younger women than those my own age, but I’ve changed” yeah.
    The difference between all your clients and Ava’s man is your clients KNOW they have a problem.   Evan, you didn’t marry the anonymous hate mail girl and she obviously felt the ends justified whatever happened, even if that’s a nutty thing to do.   It speaks more about her than about you, though if you consistently trashed her that would speak about you.
    Ava can totally say “There is no judgement about this, just a curiosity and wondering what you learned from the whole experience”.   People who are honest about their past tend to be the kind of people I’d want to date anyways.

    1. 2.1
      Chris H

      Tons of judgement. More so, age of consent is 14-18, so “this close” is relative. 1 to 4 years isn’t really “this close”.

      1. 2.1.1

        Age of consent is 14??? WHERE?!

  3. 3
    Jackie H.

    Ava…it seems like you have some growing up to do…I feel I upgrade any man that I date so…anyone before me won’t measure up anyway…lol…

  4. 4

    I can see why this gives you pause. How long ago were they married? I think the timeline matters. There are a bunch of other things to take into account here as well. Such as, how mature was the girl, where was your boyfriend in life at the time. It is kind of creepy of him to have been dating someone so young, but it happens, especially if he hadn’t found his path in life yet (was a server or something). At the end of the day though, people often make decisions they aren’t proud of and he told you about her I would assume? So, he’s being open and honest and making you happy. I think that’s all you should focus on going forward. Everyone has a past, and while his was with a much younger woman, he had a committed and long relationship with her. I would prefer that to someone who had never been serious with someone before. Plus, if I lined up ten 18 year old girls, some would look 12 and some would look 25… for some reason I feel like if she at least looked older its not creepy. And as an aside, my boyfriend (whom I’m very happy with) was with a stripper for 5 years before we met and she cheated on him multiple times. There are days when I think wtf was he thinking?!? But, it never actually affects our relationship. I wouldn’t even quiz him about it and don’t try to make him feel bad about it or shame him. There’s no point. Now, if you find out he has a bunch of 18 to 20 year old female friends, I would be concerned and talk with him about it.

  5. 5

    I used to find this issue (feeling okay about a guy who made poor choices in past relationships) a difficult one, myself.   However, I realised that it was basically a trust issue for me.   Either I trust that I’m with a good guy who’s made the occasional mistake in his past ~ as have I, and everyone else I’ve ever known ~ or I think he’s got terrible judgement and mistrust his ability to make good decisions and in that case I need to break up with him.     Continuing to date someone while constantly giving him the mental side-eye is not fair to either of you.

    1. 5.1

      we can talk more if you like,are prefer talking in private in that process are can give you all that you need,thank you

  6. 6

    The bottom line here is this: He is not with the ex any more, he is with you.
    He chose you. So why worry about the past? He has obviously learned from his mistake. Leave the past where it belongs (in the past… lol) and enjoy the present with your boyfriend.

  7. 7

    I My question would be is she the only woman who cheated on him? Or is this his pattern? Is he attracted to women who cheat?
    Have any other women cheated on him since? How did his last realtionship end.

  8. 8

    Jeez, Angie, a person might think one of your boyfriends/husbands left you for a younger woman or something…

  9. 9

    While I certainly wouldn’t want a guy to judge me for my past, I do believe I have a good answer: at one time in my life, I had low self esteem and was struggling with who I was and how to make my way in the world, overcoming an abusive mother and depending on a guy to “save” me. I’ve certainly moved past that to a large extent now. In fact, I’m a much better catch because of it: I learned to make my own life, to not take things as personally, to not get caught up in a guy’s validation. My sketchy situations with men largely stopped by age 27. So … the important thing is not exactly what happened in someone’s past, but do they have a real reason for it, can they perceptively explain why it happened and how they’ve changed or moved on to relate to the opposite sex in a healthier way?

  10. 10

    @Joe Your average 18-year old is still in high school.

  11. 11
    Sparkling Emerald

    Very good answer Evan !!!!!!
    I have a don’t ask, don’t tell policy about past relationships when dating.   Of course, much information comes up “organically” in conversation, but I don’t grill anyone about their past relationships, nor do I appreciate being grilled about mine.   At my age, we ALL have some   baggage, if you don’t, you’ve had a pretty boring life journey AFIC.   I’m not looking for someone to be my baggage handler, I prefer to store it in a neat little carry on in the overhead compartment.   The guy I am dating right now is really great about not prying into my past, he doesn’t seem to mind that I am   technically still married, anything he finds out in passing, he takes in stride with a smile (which isn’t much, except he didn’t know I was married twice until date six).   He doesn’t even seem to mind that my son has moved back in with me for the summer, he’s very friendly and understanding about it.   Such a nice change of pace from the grilling I got about my marital status being “currently separated” from the other match.comers.

  12. 12
    Sparkling Emerald

    Angie – 10 “Your average 18-year old is still in high
    school.”      I (respectfully) beg to differ.  
    Depending what year she was born, what the cutoff date for starting
    1st grade was when she started school, an 18 year old could very
    well be a HS grad, or even a college student.   I turned 18 at
    the very end of my senior year of HS, I was 18 for less than one
    month of HS, I left home August after I graduated HS.   Most of
    my time as an 18 year old I was living on my own, working full
    time,   and self supporting.   (didn’t ask for a dime from
    Mom & Dad) 18 is the legal age for being an
    adult.     While the age gap is pretty big, (18 &
    24) his ex was a LEGAL adult when the relationship started, it is
    unknown if she was in HS when the relationship started and for how
    long, and she was 23 when they married.   I really don’t see
    much to raise an eyebrow about,   except that SHE cheated on
    HIM, so how is that his fault ?   (well we really don’t know
    what led her to cheat, but I would give the cheated upon person the
    benefit of the doubt)

  13. 13

    I agree it’s best to leave the past in the past. God knows,
    I’ve certainly had my share of wacko relationships based on poor
    judgment, neediness, and the denial of blatant red flags. But Ava’s
    guy’s “baggage” is different from the examples Evan gives. In
    short, there’s a creepiness factor I would have a very hard time
    getting beyond. It’s not so much the age difference that bothers me
    about this situation, but the fact that his ex was
    18 when he met her. He was almost
    twice her age and had already lived a substantial amount of adult
    life, as compared to her barely legal, possibly still in high
    school stage of life. I don’t care how mature she was, how
    “womanly” she looked, or how immature he was. What 18 year old girl
    has her head on straight enough to be able to negotiate a serious
    relationship or stick up for herself with someone so much older? At
    18, you’ve got a whole lot of transformations and reinventing of
    yourself to go through before you even begin to know who you
    actually are as an adult. And it isn’t like he made a mistake and
    slept with her once in a moment of poor judgment, maybe drunk, and
    not realizing how much younger she was. They had a 5-year
    relationship and then he married her! If my daughter had been
    dating a 34 year old when she was 18, I’d definitely question the
    guy’s integrity. At best, it shows poor judgment or lack of
    self-esteem on his part; at worst, it’s just plain creepy. But it
    doesn’t matter what I think, it only matters what Ava thinks. I
    take her at her word that it’s unsettling and she is having doubts.
    She doesn’t state in her letter that he was forthcoming with this
    information…she only says that she just recently found out about
    the age difference. It bothered her enough to write about it, and
    if she’s going to always be wondering about it, that’s not gonna
    work for either of them. Without falling into paranoid what
    if’s, if she’s got doubts about his ethics or trustworthiness,
    that’s going to be difficult to overcome.

  14. 14

    [email protected] and [email protected]: And your average 18 year old either works at a McDonald’s or at the mall or doesn’t have a job at all. Not sure how a fully grown male with a job/career negotiates that one. Or the work parties or family gatherings with the teenage girlfriend in tow. And what do you talk about. And what 18-year-old wants to bring some old guy to her teenage things. Creepy.
    (One of my friends from college brought her 40+ boyfriend du jour to our other friend’s wedding, and he walked around all day trying to fit in with us then-25 year olds. In all of our pictures from the day there are all of  the college friends and then  this creepy old guy  in his dark sunglasses lurking over our shoulders. None of us ever even knew his name and our friend didn’t date him for very long. Really, this old guy had to ruin  these  photos of our youthful fun times because he had some weird personal crisis going on and our friend was insecure and easy pickings.  Disgusting.)

  15. 15

    Of the mistakes women often make in relationships, getting too hung up on their boyfriend’s ex/exes is the silliest.
    Who we dated or were in a relationship with once upon a time says almost nothing about who we are today. It really is crazy to come to conclusions about a person, when you don’t know the circumstances of the relationship, what the relationship was like, or who the two people involved were at the time.   As long as she is truly out of the picture, I would absolutely forget about it and move on.
    My first husband was a pathological flirt, yet I gave him a chance because I sensed it was only a surface thing, and that he was actually really looking for his “the one”. He turned out to be the most wonderful, supportive, *faithful* partner.

  16. 16

    Anita #14
    One of my friends from college brought her 40+ boyfriend du jour to our other friend’s wedding…Really, this old guy had to ruin these photos of our youthful times because he had some weird personal crisis going on and our friend was insecure and easy pickings. Disgusting.
    Wow — judgemental much? For the life of me I can’t understand why we just can’t let people date whoever they want without judging them, or inferring they’ve got issues or are insecure.
    I’ve always been bemused and perplexed when I read comments on websites from women disparaging guys who date younger ADULTS (particularly the Daily Mail about Leo DiCaprio, Bradley Cooper, Jeff Goldblum etc.) At first I couldn’t understand why anyone cared, until I realised what you are trying to do — you are trying to stigmatize them for the same reason that men used to stigmatize women in previous generations — you are trying to control their behavior. Men used to call women ‘sluts’ to shame them from sleeping with other men, thus reducing the chances that they’d get impregnated by those men. You are trying to stigmatize men because you have a latent fear that they will dump you for a younger model.
    Jeez, why can’t we just live and let live. Ruin your photos? Please, who’s to say you haven’t ruined everyone else’s photos?
    Regarding the op – secure people don’t care about someone’s previous dating history and they have the wherewithal to assess the person on their current merits, not their past. Worrying about these things is a classic sign of insecurity and almost gives him grounds to dump Ava.

  17. 17
    Sparkling Emerald

    Anita 14
    [email protected] and [email protected]: And your average 18 year old either works at a McDonald’s or at the mall or doesn’t have a job at all.
    I don’t believe the 18 year old’s job OR HS status was mentioned, so let’s not assume facts to fit with your biases.
    !8 years is a LEGAL adult.   No statutory rape here.   I got a part time job as an apprentice printer March of my Senior year.   The day after HS, my job went full time,   often it was with overtime.   This was no part time or burger flipping job.   I fully supported myself at age 18.   Some other 18 year olds   joined the military. Some of my other 18 year friends worked their way through college, others had college paid for by their parents, some went straight to work, but still lived at home etc.   Some married their HS sweethearts.   Try averaging all of the 18 years old in my age group together, and what you get is a MEANINGLESS composite.   We all should be judged as individuals, assumptions based on “averages”   tell us nothing meaningful.
    And I agree with Evan, let’s leave the past in the past.   I certainly don’t want to be judged or grilled for my past.   Unless someone I’m dating was a serial murderer or serial rapist or robbed banks, I’m not going to be concerned.

  18. 18

    My take on age differences is that they matter much more at the younger end of the age spectrum, and less as the ages increase. A 40 year old with a 56 year wouldn’t raise much of an eyebrow, but an 18 year old is barely out of childhood, too young for a 34 year old man. If I had an 18-year-old daughter, i wouldn’t be happy about her relationship with a man so much older, and I’d question his motivations. I’m wondering if Ava is concerned that her boyfriend has a “thing” for much younger women, and if he might stray with someone younger, even if he seems happy now.
    Although I try not to judge people I’m dating on their past relationships, I do like to have some indication that the person has actually learned from their past mistakes. I think this is especially important given the fact that the divorce rates for second marriages are higher than for first marriages, and even higher for third marriages. Angie’s post (#2) makes sense to me. In other words, the ex shouldn’t necessarily be a deal breaker, but something to ask questions about.

  19. 19

    ^ All I was saying is, the average 18-year-old doesn’t have a lot of life experience. I know people who have married their high school sweethearts, my brother included, and I know a 19-year-old who I would say is very mature FOR HER AGE.   I’m 31 and we can have lunch and relate on certain levels.   The 30-something men who want to date her… not so much.
    I don’t think this means that Ava’s boyfriend is not in a different place and should be judged, but I do understand why it raises some eyebrows.   If someone told me their ex cheated and it ended, I’d take it at face value, but if in Anita’s place, I probably just would’ve said “What did you have in common with a teenager?”   Her new man is clearly open to speaking about it.
    Just because something is legal doesn’t mean there is not a creep factor associated with it.   If you found your new man was a videographer for porn or something like that, would it also raise eyebrows?   It’s worth a conversation just so Anita feels comfortable and secure, not because she should hold this man accountable for who he was 8 or 10 years ago.

  20. 20

    I see 18-year-olds every day when I drop my son off at his high school. I honestly cannot envision any of them with a 34-year-old. Even if she was not a high school student, but a very mature, for her age, college freshman or fast-food restaurant employee, that still doesn’t make it right. 34 and 18 is still pretty mind-blowing to me. I agree with Jenna, Angie, Ruby and others who suggest that maybe it is time for Ava to have a more detailed conversation with her boyfriend about how that relationship came to be in the first place. Six months isn’t enough time to get to know a person well. Maybe there is indeed a side of him that Ava is just finding out about. Is he a decent guy who made an honest mistake or a modern-day Humbert Humbert? Could be either, she doesn’t know at this point.

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