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. 81

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

  2. 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….

  3. 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!!  

  4. 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.

  5. 85

    Well said Evan!!!

  6. 86

    After all we are all humans and we make passion mistakes

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