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. 21
    Karmic Equation

    The 18yo was probably hot and he probably couldn’t believe his luck in having an 18yo hottie be open to his advances. Then she probably pressured him to marry her, so he did. She was probably more in control of the relationship than you might think, particularly if she was super fine.
    As much as most women deny it, it’s the unfortunate truth. Most men are easily controlled by his lust of a beautiful woman, especially beautiful YOUNG women. So don’t blame him but blame his…uh…equipment. And give the 18yo her due and him a mulligan.

  2. 22

    Karmic @21
    I totally agree with you. Most guys, me included, would date a super young hottie given the chance. The reason is because dating someone almost half your age that is fine looking comes around rarely in your lifetime. If that happened to me, I would milk it for all it was worth even though I know she would probably dump me in time for someone closer to her age.

  3. 23

    John @22,
    Dating younger women? this is easily done by targeting mail-order-brides from a foreign country. An ex-bf of mine has married women half his age TWICE in the last 15 years: the first one, a 25-yr old Russian beauty, got out when she got her US citizenship. He took a short break, switched to China and just married another woman 20-something years younger. She is cute, slim, and 42. He is 65. You know what he said when I asked him if he truly believes this will last? (We stay in touch occasionally). Amazingly, he said, quote, “we’ll, it will last for SOME time”…

  4. 24
    Sparkling Emerald

    OK, OK, so let’s say this guy was totally CREEPY, WRONG & PERVERTED, for getting involved with a legal adult and marrying her 5 years later.   Feel free to throw stones at him if you’ve NEVER made a relationship mistake. NEVER fell in love with a F-Buddy, NEVER let yourself be in relationship limbo for years on end, never been divorced, never broken an engagement, never said “I love you” to someone,   then dumped them,   never had a one night stand that you regretted, etc. etc.   It’s IN HIS PAST !!!   I agree with Evan.   We’ve ALL made mistakes, unless of course we’ve never really done any living to begin with.

  5. 25

    [email protected]: Read  [email protected]. Keep this in mind. Then imagine a small, outdoor wedding of mostly 20-somethings who have known each other for about 8 years. Have gone through university together, moved into adulthood together, spent long nights studying and working together, have travelled together. Then imagine a guy, almost 50 years old, in large dark shades that he never takes off, who is there as the date of a woman about half his age whom he has been dating only a few weeks. This is not some big blowout wedding with a hundred relatives whom no one knows. And there is no one else there his age. Then imagine him always popping up in those large dark shades when one of our friends, the art photographer, is trying to document the wedding, trying to get  loving shots of these close  friends and the first day of  marriage of this young couple. And why is this guy there again? Read [email protected]. Perhaps you owe me an apology.
    [email protected]: Well, the average 18 year old does work at a fast food restaurant or at the mall (or, will add, some other kind of very low-skill labor) or doesn’t work at all. And most people graduate HS at 18. So it isn’t really a bias to state what is the experience of most 18 year olds.  It’s just stating an observable fact of the world we live in. But you’re right–we’ve no idea what this guy’s ex did. Maybe she was one of those folks who graduated HS at 16 and was a surgeon by 18 or had launched some other similarly stellar career and she really was the financial, emotional, professional, intellectual,  sexual  equal of the guy. I think the OP probably would have mentioned some very curious fact like that, but could be wrong. And why are you bringing up statutory rape?  Ew.     

  6. 26

    Sparkling Emerald #11 & 17 & 24
    Well said!! You are a gem!   🙂

  7. 27

    @Anita   Yeah, he is weird that he never takes off his shades. Hmm..a bit strange that he was trying to get in the pictures with the circle of friends if no one else from outside that circle (other people’s dates?) were or did they?

    Why is this guy there?   BECAUSE HE WAS INVITED! Your friend invited him to come. It is on her. All he did was show up and try to enjoy himself. Someone might judge your friend for inviting a complete outsider who was a bit of an antisocial boor, but not the boor she invited. Those someones would be the bride and groom, not you.

  8. 28
    Sparkling Emerald

    Anita 25 ” And why are you bringing up statutory rape?  Ew.    ”
    Because Angie @ #2   accused him of being   very close to statutory rape, even tho’ an 18 year old is a legal adult. And most states consider statutory rape to be with a consenting minor under the age of 16, and some states even under the age of 13.   By Anita’s logic, a person who buys a drink in a bar on their 21st birthday is coming “this close” to underage drinking.
    Look, I never said she was a brain surgeon, just pointing out that when someone graduates at age 18, the rest of their time as an 18 year old is that of someone who is NOT in HS. It seems some posters have to make this worse than it really is, by speculating the worst, she was a HS student/burger flipper, even tho’ those facts are unknown. First grade starts at age 6, 12th grade starts @ age 17, post HS usually starts at age 18.   I was 18 for less than 3 weeks of HS.   The relationship STARTED when she was 18, and they married at age 23.   So even if she spent her ENTIRE 18th year as a HS student, she wasn’t a HS student for the 7 years or so years of the relationship.
    I’m not saying that a 34 year old dating an 18 year old, then marrying her at age 23 is the most fantastic relationship in the Universe, but I am curious as to why THIS relationship is considered so taboo, but F-Buddies, one night stands, verbally abusive relationships, limbo land undefined relationships, and every other kind of bad relationship we read about on this blog, doesn’t seem to raise as many eyebrows.  
    Have you NEVER made a relationship mistake ?   Can you cast the first stone ?
    We haven’t even heard about this relationship from either person who was in it, just the next girlfriend who thinks this could be a deal breaker.   She must be an exceptional person to have NEVER had made an unwise relationship decision.   Perhaps she should dump his sorry but, and find her equal, someone who walks on water just like her.

  9. 29

    I’m with Goldie.   Most 18-year-olds would completely grossed out by any 34-year-old.   I, too, would wonder how it came to be.   She was still a teenager for goodness sake.   There are stalker-type men or teachers who get involved with students.   If I were this reader, I’d check to see if that happened in the past.   If it is his pattern and he hasn’t gotten serious therapy to deal with it, I would bet money he’ll try it again.   Trust me   — I lived with someone like that.

  10. 30

    Perhaps the tone of my comment was a bit harsh but I stand by the essence of what I said. At 25 your friend was not a child and was a fully functional adult capable of making her own decisions – it is not your place to judge those decisions. As her friend you must accept whatever she decides and not judge her for it. It was unfair of you to imply that he was having a crisis and call him ‘disgusting’. The sunglasses, the age-gap, being friends for 8 years and the fact the wedding was small are all irrelevant — what’s relevant is that it is your friend’s decision who she brings and you must accept that.
    Regarding John ‘milking’ her for all her worth? Adults can only be milked if they allow themselves to be — perhaps she was milking him for all he’s worth? I think you put too much stock in thinking that guys are some kind of Machiavellian puppeteers manipulating innocent young women. We are not that clever and grown women are not that helpless.

  11. 31

    Zina @23
    Dating younger women? this is easily done by targeting mail-order-brides from a foreign country.
    Not quite. Dating someone who uses you to get a green card somewhere down the line is not what I am referring to. Sure, anyone can do that. But if you get a young hottie using that method, it doesn’t count.
    Anita @25
    [email protected]: Read  [email protected]. Keep this in mind.
    Not sure how my comment is a good defense in your argument against Tom. I understand his point fully. And I don’t agree with yours. So please don’t hijack my comment to justify your position.

  12. 32
    Sparkling Emerald

    Anita 25-
       I question a wedding where as you claim there was NO ONE the age of the 40 something year old.   Were the bride & groom orphans ?   Why were there no parents, grandparents, aunts & uncles at this wedding ?   Why is it a crime to wear sunglasses at an OUTDOOR wedding ?   I think a bride & groom who ONLY invite their 20 something year old friends and don’t include family members is a bigger issue than a 40 something year old guest wearing sunglasses and “spoiling” the pics.   How shallow to consider a wedding nothing more than a photo op for the young & the beautiful.  
       The art photographer could have asked for some posed pictures of the “old gang” or something.  
       Would you have been disgusted if this was a more normal wedding that included multi-generational guests if a parent, grandparent, aunt, uncle, 40 something friend of the family wore sun glasses and hung around at the wedding ?
       Tom10, I agree with your take on this.   I don’t think your tone was too harsh, especially coming from someone who doesn’t think a 25 year old woman is capable of making her own decisions, and apparently, thinks it’s “disgusting” to wear sunglasses outdoors.

  13. 33

    “And there is  no one else there his age.”
    What about the parents of the bride/groom? :-p

  14. 34

    @ Anita: “Then imagine a guy, almost 50 years old, in large dark shades that he never takes off, who is there as the date of a woman about half his age whom he has been dating only a few weeks.”
    Ah, therein lies the problem. How did this guy end up on a guest list for a small wedding? This is a wedding etiquette error, not a dating error IMO. She could’ve brought someone her own age she’d just met a few weeks ago and he could’ve been a bad fit at that wedding just the same. Of course, at 50, you’d think the man had been to enough weddings in his life to ask himself, Should I be a guest at a wedding of a couple I don’t know, just because I happen to have been dating one of their friends for a few weeks?
    Regarding John’s comment, hmm my advise would be, do not milk, lest ye be milked. If you get into a relationship with the intention just to “milk” them for their age and looks, don’t be surprised if she milks you right back for your status and money. Personally, I prefer my own peers, but that’s me.

  15. 35

    As far as the “statutory rape” comment goes, in many states the legal age of consent is 18, although it does go as young as 16. So 18 is legal – barely – which was Angie’s point, I think.
    But as far as the older guy at the wedding goes, he was an invited guest, so he had the right to be there, creepy or not. If this was such an intimate affair, why invite the older guy in the first place? Although, maybe he should have stayed out of at least some of the photos…

  16. 36
    Karmic Equation


    I’m with AllenB. Your outrage is misplaced. The 40yo wouldn’t have shown up at your friend’s wedding if his date hadn’t invited him. If you want to be angry at someone for “ruining” a memory, be angry at your friend who invited him. And I’m going to go out on a limb and say it’s likely at 40, he paid for the hotel room, the travel arrangements, the drinks, so basically your friend attended the wedding for free. Who’s milking whom in that scenario? You’re giving your friend a free pass while painting him as some sort of villain. I disagree with that POV.

    Tom10 @ 30 summarized it best:

    [Men] are not that clever and grown women are not that helpless.

    While most 18yo girls may not have enough life experiences to make good decisions, believe me, 18yo non-virgins know EXACTLY how to use sex to get what they want.

    I have a friend who was entrapped by a 16yo girl (when he was 19yo) into a relationship, by deliberately getting pregnant. While he never married her, he spent the next 18 years with her, fathering more children, so she could live off welfare. Getting on welfare was her job. Her mother, aunts, basically whole family is on it.

    She never wanted to work, welfare was her ticket to an easy life as she saw it. At 16, she knew what she wanted and she got it. She knew what she was doing when she got pregnant. While you and I and others who are more educated or more privileged are aghast at her choice, there are many women who don’t think of being on welfare as a stigma. They think of it as a free ride and take particular pride in gaming the system.

  17. 37

    “secure people don’t care about someone’s previous dating history. ”
    Secure in what? Youth and hotness and being left for a younger hotter girl? What has insecurity got to do with it? Let’s face it everyone grows older and there are always going to be younger and hotter girls as we get older. So what? Any man who is only interested in a womans youth and how hot she is or places that as a priority hasn’t really   proven or shown he has any depth of character and is able to be in a grown up loving realtionship, or goof future potential realtionship material. He has shown the complete opposite that he is highly unlikely to be a man of charcater and care about who the woman/girl is.   Objectifing women on their outer surface level appearance. Any woman who cared about her heart health and happiness would be wise to not get involved with someone like that.
    I would say that people who do not care about learning about potential partners previous history haven’t yet learned to take responsibility fort their own health and happiness. And the ones that are curious in learning care about their own health and happiness are wise and sensible   to find out about a potential   future partners relationship and dating history in order to see if they are a good realtionship match now. And to listen carefully to what they are saying now about these previous relationships as this will tell you quite clearly where they are at , if they are stuck repeating over and over the same mistakes that didn’t work or if they have grown developed, moved on and are now at a place in their life to WANT and be ABLE to do the type of relationship that MATCHES what you want.

  18. 38

    Goldie # 20
    I may not always agree with you but I look forward to what you have to say because your posts are well thought out and usually very fair.   I also do NOT get the feeling that you come from a place of hating men. Beyond that I have read your stuff and more than once had an “Ah ha” moment.   I have to admit that the age thing pushes my buttons too,    (but that is my issue).   When I look at my past, I know that I made decisions based on who I was at the time and I can not be the one to “cast the first stone”.   
    Who is he now?   What kind of a man is he now?   He did not become the stepfather of a twelve-year-old girl in order to seduce her.   The Humbert Humbert reference was not fair .   But I agree that six months with someone is not enough time to know them well.   She should let his actions NOW speak to who his is in the present.
    Sparkling Emerald # 28
    Again well said!   

  19. 39

    Oh, another missing piece–the friend who brought this winner to the wedding had been date raped just a little while before–she’d been a virgin. After that her behavior changed in a most disturbing way; we all noticed it and yes, we did not appreciate her bringing this opportunistic p*ssy chaser to the wedding at all. I might have mentioned all this before but I hesitated, given previous threads about how women who are raped should just get over themselves. Based on those previous threads I do not expect any understanding from the main readers here on that one, but perhaps those of you who are inclined to understand will understand.
    But let’s switch it around a bit, in the hopes that you will gain some understanding. Let’s say there’s a bunch of nerdy Jewish guys who all went to college together. They’re naive and inexperienced around women, sheltered, from traditional middle class homes. A really hot “older” woman–meaning (on this blog) that she’s two years older than he is–starts showing one of the guys a lot of attention, and encouraged by his friends, all eager to start dating, he asks her out. On the date he is very thoughtful, generous, as he has been taught to be on a date. But at the end of the date she starts manhandling his privates, jerks him off against his will, and steals his wallet. This is his first “real” date. None of his other friends have ever been treated this way and can’t fathom it. He doesn’t talk much about it–word just slips out among the concerned friends. Then one of the guys–a little more advanced on the relationship spectrum–has a sweet girlfriend he’s  been dating for years, and  they get married shortly after college. They invite just their closest friends to a small ceremony on a bluff overlooking the ocean because they don’t have much money. The guy who was psycho-raped/robbed brings as his date a 50 year-old woman, recently divorced, who wears a low-cut mini dress, ignores all of the young women at the wedding, flirts with all the nerdy young guys, and is always touching the guy she came with, even though no one else is acting that way, and she’s always trying to get in the photos with the young nerdy guys, wearing a phony, “I’m so cool grin.”
    You really think that  this is merely about being “judgmental” of May-December romances and trying to “control” male behavior and that just “accepting” the abuse and exploitation of others is the way to be a good friend? Again, I use the same punchline as always. It’s a human thing, not a gender thing. I urge you to think about it.

  20. 40

    Anita @   25
    I completely understand that the older guy contributed the creepy factor to the equation but was it really his fault?   He just accompanied the woman he was dating (by mutual consent) to an event because she had requested his presence.   I think this says a lot more about your friend than it does about him.   I don’t know the details so I won’t deny that she was vulnerable or that he was a creep but I still don’t understand how you can fault him for the wedding.   I almost feel sorry for him.   Imagine being in a crowd of 20-somethings, knowing that you don’t fit in and not being able to do anything about it.
    As to the letter from the OP, it doesn’t matter whether it is “okay” for a 34 year old to marry an 18 year old.   The fact is, it happened.   Can she live with it?   The question is not “should she judge him?”.   She already has.   The only thing that remains to be seen is whether or not she can get past it.   Asking questions about why it happened and understanding the circumstances may help.   She has provided no background information so it’s really hard to say whether or not this man has a problem or whether he just made an error in judgement.   The discussion about whether a person’s past is relevant is pretty moot.   There are equally strong voices on either side of the discussion but both are just opinions and neither will help this woman!

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