Should I Judge Him For His Last Relationship?

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.

Join our conversation (88 Comments).
Click Here To Leave Your Comment Below.


  1. 61

    Post 54 my mistake was in response to Tom not Karl.

  2. 62

    My husband is a full ten years older than me. I’ve lost count of the number of times people have asked us if we met at college. (I’ve also always been told I look young for my age, so go figure.)
    As to the original question: people date and even marry across large age gaps all the time, and funnily enough, people get divorced all the time too. Should you judge him on his last relationship? Only if you were the woman involved, otherwise it’d make far more sense to base any judgements on what’s in front of you now. Does he leer at schoolgirls, seem juvenile, come off as creepy? No? Then his past isn’t throwing up any red flags that I can see from here.

  3. 63

    @ Sparkling Emerald # 59
    You raise some very good questions.  I agree that it seems odd that this sunglass wearing guy was the only “old” guy there.  But then perhaps this wedding took place in Never Never Land and adults couldn’t come… except pirates.  Hmmm… maybe sunglass dude was a pirate.  Well that explains a lot!!  That the wedding photographer did not know how to actually be a wedding photographer could also be explained.  How can you expect one of the Lost Boys to know how to take pictures?
    And in Never Never Land NO ONE wants sex so I can see how sunglass dude/ pirate would stand out with his nefarious intentions.

  4. 64

    “Maybe he’s not the person I think he is?”
    You have your answer, your gut instinct is telling you something is off. 


  5. 65

    Anita #57
    I’m really sorry for your friend’s experiences.  That really sounds awful.  I’m not denying that the guy might have been a creep and that your friend was not exactly in her right mind and was possibly taken advantage of.  However, none of that has an impact on the question at hand which is – who takes responsibility for the creepy guy at the wedding?  At least from what I have read, he received an invitation from the woman he was seeing to accompany her and agreed to attend.  Maybe he did know he would be the only 40-something there and maybe he didn’t.  At the event he behaved like a total boor.  This is the ONLY thing he can be blamed for with regards to this question.  Whether or not he took advantage of your friend, whether or not he was just in it for the sex, how old he was,etc, etc are all irrelevant topics.  Your friend should not have issued the invitation given the nature of the event and if she wasn’t in her right mind then someone else (perhaps bride) should have made the decision for her.  I’m very sympathetic because I can understand how he may have ruined an intimate event.  It also sounds like he behaved very badly (I took your description of the hypothetical woman’s behaviour to be the way this man actually behaved) but again, your friend enabled his behaviour.  If he hadn’t been there, and it sounds like he really shouldn’t have been, he wouldn’t have had the chance to behave badly.
    @Lia & Sparkling Emerald
    What’s with the irrelevant questions about why the bride & groom chose to have only 20-somethings at their wedding?  It doesn’t matter.  It was their wedding and it was their choice.  If you read one of her earlier comments, she DID sort of address this.  Also irreverent comments about the photographer were unnecessary and pure conjecture.  It sounds like the 40 year old tried a little too hard to fit in, consistently poked his nose where he wasn’t wanted and wasn’t on his best behaviour which is the problem.  There’s absolutely no excuse for that.  But none of this is relevant to the original question – why was he there in the first place?  Because he was invited and given the opportunity to display his horrible manners.  The invitation was not his fault.  I think we are at least agreed on that.
    40 (or mid to late 40s in this case) is not old but it can seem so to a 20-something.  “Oh yeah, I’ll probably do that when I’m old…like 40.” 🙂
    We’ve all said it.  I’m 30 years old now so “old” is no longer someone in his/her late 40s but someone in their late 50s, hehe.

  6. 66

    # Lia #61: maybe his belt also failed to match his shoes! (oh the horror!)
    Anita, when Demi Moore got married to Ashton Kutcher, were you thinking to yourself, “That bitch should leave him alone; Ashton is so young and naive!”?

  7. 67

    Sounds traumatizing for the bride and groom. I certainly hope no disabled people who might have been invited had the audacity to actually show up, attempt conversation, and ruin those wedding photos of flawless twenty something year olds.  

  8. 68

    You know, we are also assuming that his ex was just a normal, lived in America all their life teen. What if she wasn’t? What if this girl is world traveled and had an awesome job? It isn’t actually impossible. What if she’s from a country where its standard to date someone much older? I knew a Ukranian girl once and that girl exclusively slept/dated much older men. She had zero interest in guys her age. It was much less weird than someone who had just graduated high school and had never had a job and was living with their parents. I think this is about much less the age and more the life circumstances. I think it is rare foran 18 year old to be really mature, but I don’t think its impossible.

  9. 69

    Joe #  67
    I didn’t even think about that!  Surely he wouldn’t go that far!  Then again it was said the guy was looking to score with his date so he was probably the kind of guy to wear a belt that didn’t match his shoes.  What is the world coming to?
    @ Shaukat # 68
    OMG!! Anita and her friends would have been scarred for life!!!  

  10. 70

    Scaramouche #66
    “40 (or mid to late 40s in this case) is not old but it can seem so to a 20-something.”
    Then what does 70 seem like to a 20-something? There’s a difference between “older” and “old”.

  11. 71

    Laugh! All I will say further on this topic is that you all have gone off the deep end! What you all are saying has absolutely nothing to do with the reality of that day, that time, or those people!! There must be some mighty fine Kool-Aid around here!

  12. 72
    Karl T

    If the guy were George Clooney, would he still be a creep?  Do you like being called a slut?  No, right?  Most women don’t like slut shaming.  Why the creep shaming then?  Hypocrites bother me….

  13. 73

    Karl T: I couldn’t care less what people call me. Call me a feminist, a slut, judgmental, a creep, a hypocrite–whatever floats your boat. Shame, attack, slapdown, bully, banish, patronize, criticize, and rant away!! 🙂

  14. 74
    Karl T

    If the guy were George Clooney would he still be a creep?  You failed to answer the main question.

  15. 75
    Sparkling Emerald

    Anita – You are the one name calling and ranting.  You have been going on and on about an invited guest being the wrong age & wearing sunglasses outdoors.  I guess his other crime was socializing at a social event, when in your view, and apparently the view of the shallow bride and groom, he should have sat back in the corner and ignored everybody.  Sounds like a very shallow affair, being thrown by a very shallow couple.  Do they plan on having children ?  Do they plan on attending the weddings of their future children, or will they do the “right” thing and not intrude on their children’s special photo op ?

  16. 76

    Wow, a lot of insightful posts here! To answer a few questions:
    They began dating when she was 18 and the relationship lasted for 7 years.
    They were both in college at the time (he was pursuing his masters degree). I would not say he’s immature, but definitely “youthful”, and a bit of a late-bloomer.
    She pursued him and she asked him to marry her (he agreed because he was in need of a green card).

  17. 77

    Kart T: Yes.
    Emerald: I never engaged in name calling or ranting. I said in post 14 that the guy was “creepy.” EMK used the same adjective here: “18-year-olds are children and it’s super-creepy and questionable behavior on the part of a 34-year-old man.”

  18. 78

    Aha!  That hardly seems creepy.  Perhaps a bit opportunistic on his part, to get a green card (but who wouldn’t take that opportunity, if presented?).  If she pursued him, it’s as creepy on her part as it is on his (which, IMO, isn’t very much at all).

  19. 79
    Karmic Equation

    Anita 78
    I think you got your interpretation of “never” comes from the same place you got your interpretation of karma.
    Your posts at 14, 25, 39, and 57 contained rants. Even #74 could be considered a rant.
    1. to speak or declaim extravagantly or violently; talk in a wild or vehement way; rave: The demagogue ranted for hours.
    Did you find this info out after you submitted the letter? If you had, I think the comments on this thread would have had gone differently.

  20. 80

    @Karmic Equation
    I was aware of this information at the time. I don’t know any specifics (other than school) as to how they met, but his words were “she was insistent”.

  21. 81

    Ava, putting logic and reasoning aside. What does you gut instinct say?

  22. 82

    Karl,why are you so hung up on George. He is nor that great looking.  I don’t know why men especially older think so. No woman my age that I know (22-30 ish) think so. I bet if the roles werereversed and a woman you found unattractive was learing over you and your friends all neck would break loose. Calling the male creepy is not the same as slut shaming. Give me a break. If I am invited somewhere I could be out of place. I turn down the invite. I have had friends who don’t think first and invite me to their famalies receptions. I am smart enough to know that I would be out of place with a bunch of family. Yes 4 plus is old to people in their 20’s….shocker. I don’t think so,but many do. Clooney is not that great or even seemingly into women anyway….

  23. 83

    Hi Ava
    I met a man when i was 18 and he was 34.  Two years later we married. Three and and half years later we had our first child and would have two more within a few short years. He was immature. He never helped me and when i was 34, I wondered what the hell he was doing with an 18 year old when he was 34!! His family never liked me because i was too young–not that he was too OLD!!  
    Any 34 year old man with an 18 year old is immature otherwise they would be with someone their own age. Maybe too broad of a statement but those are my thoughts. When i turned 35, i wanted to separate which we did much to his horror. Two years later we divorced. Right away he married someone his age.
    Don’t judge your husband. He made a mistake. That’s all.  Now he has you. Happiness I’m sure!! 

  24. 84

    I disagree.  I think someone’s relationship history gives you huge insight into them as a person.   And I’m sorry a 34 year old with an 18 year old is just creepy.

  25. 85

    Well said Evan!!!

Leave a Reply

Your email address will not be published. Required fields are marked *