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.

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  1. 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.

  2. 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.

  3. 33

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

  4. 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.

  5. 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…

  6. 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.

  7. 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.

  8. 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!  

  9. 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.

  10. 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!

  11. 41
    Karl R

    Ava said: (original post)
    “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.”
    Let’s turn this around. What if he had shown impeccable judgment in his past relationships. He’d found and dated someone who was wonderful and they’d managed to have a terrific relationship.
    There’s a word to describe men like that. They’re called “taken”.
    By the time I was out of college, my dating pool was mostly made up of people who had checkered relationship histories. The few exceptions seem to have gotten weeded out in their 30s. You can either date people who have made some questionable relationship decisions, or you can stop dating.
    Or I suppose you can date 18 year olds, who might not have had time to make poor relationship decisions (yet).
    Sparkling Emerald said: (#28)
    “It seems some posters have to make this worse than it really is, by speculating the worst,”
    I agree. There’s no shortage of examples of that.
    A few examples of speculating the worst:
    Angie said: (#2)
    “A 34-year-old is thisclose to committing statutory rape by getting involved with an 18-year-old.”
    Ava stated they met when the ex-wife and got married at the age of 23. She does not mention what age the woman was when they started dating or when they had sex.
    I met one of my girlfriends when she was 18 and I was 27. I started dating her when she was 23 (by which time she’s already been through a marriage and a divorce). She was 24 when we first had sex. (We can probably safely assume that Ava’s boyfriend had sex with his ex-wife before she was 24, but anything else is speculation.)
    Angie said: (#2)
    “No 18-year-olds are mature,”
    In my experience, there are rare individuals who are substantially more peers. Based on my observations, they act decades more mature about 95% of the time, and they act their age 5% of the time.
    Ava doesn’t know whether the ex-wife was mature. Angie doesn’t know whether the ex-wife was mature. And since I’ve never seen immaturity listed as a reason for infidelity, I’d say we’re lacking evidence one way or the other.
    Zann said: (#13)
    “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?”
    For a couple of years I sang in a men’s choir with a broad age range (teens to 70s). When the regular director was absent for rehearsals and performaces the 15 year old stepped in as the director. He successfully led men who were two to five times his age, including his own father.
    Are you going to claim that teenage boys mature faster than teenage girls?
    Rose said: (#7)
    “is she the only woman who cheated on him? Or is this his pattern? Is he attracted to women who cheat?”
    Unless you’re living in a novel by Nathaniel Hawthorne, cheaters don’t wear scarlet letters. I’m attracted to women. Some of the women I’ve been attracted to turned out to be cheaters. Given that most cheaters actively try to hide that character flaw, it’s impossible to pursue/avoid people with that flaw.
    Karmic Equation said: (#21)
    “he probably couldn’t believe his luck in having an 18yo hottie be open to his advances.”
    Are you sure he made the advances?
    A few years ago, I got the distinct impression that an 18 year old woman at the dance studio was interested in pursuing me (I was 39). A year before a 27 year old woman quite blatantly pursued me (we dated for several months).
    My wife is 16 years older than me. I’ve had two girlfriends who were 11 years younger than me. I don’t pursue women because of an age gap … but I might pursue them despite the age gap. (I decided against trying to date the 18 year old because of the dissimilarity in life experiences.)
    Several years ago I had a coworker whom had pursued older men from the time she was a teenager. These men didn’t have to hunt her down. She was going to venues where the men were 10-20 years older and chatting them up.
    Some younger women pursue older men (either because they’re older or despite their age). Is a man creepy for deciding that he likes a young woman who is interested in him?
    Anita said: (#14)
    “what 18-year-old wants to bring some old guy to her teenage things.”
    That coworker took her 27 year old boyfriend to her senior prom. He didn’t want to go, so she bribed him (with sex). 16 years later she didn’t seem to regret that decision (though she did seem a little embarrassed to discuss it with her coworkers). And while I didn’t have the impression that she was mature for her age, I did get the feeling that she was doing exactly what she wanted.
    Anita said: (#14)
    “One of my friends from college brought her 40+ boyfriend du jour to our other friend’s wedding,”
    Anita asked: (#25)
    “And why is this guy there again?”
    You already answered that question. Your friend brought him.
    Anita said: (#14)
    “her 40+ boyfriend du jour”
    Anita said: (#25)
    “imagine a guy, almost 50 years old,”
    This man has gone from “40+” to “almost 50” in just two days. Damn he ages fast.
    Was the wedding more than a week ago? Given his accelerated aging, maybe he was in his early 20s a couple weeks ago.
    Anita said: (#25)
    “imagine a small, outdoor wedding”
    “imagine a guy, […] in large dark shades that he never takes off,”
    He’s creepy because he wears sunglasses outdoors?
    I wear sunglasses outdoors. I wear sunglasses to outdoor weddings. I have light sensitive eyes. I wear sunglasses when it’s overcast. I would wear sunglasses in my office (fluorescent lights are a bit too bright for me) except judgmental people like you consider it to be creepy.
    Apparently I’m being creepy when I wear my sunglasses outside too.
    Anita said: (#25)
    “there is no one else there his age.”
    Did your friend explain that to her boyfriend du jour before she brought him to the wedding? Or did he figure it out when he got there?
    Anita said: (#14)
    “and he walked around all day trying to fit in with us then-25 year olds.”
    Was he supposed to avoid fitting in for the entire day?
    My wife and I are talking about going to her 40th high school reunion. It’s possible that I’ll be the youngest person there. I’ll certainly be younger than any of her classmates. According to the rules of social etiquette I was raised with, I should try to fit in with these people who aren’t my age. Why do you find it creepy for me to do that?
    You’re coming across as uptight, intolerant and judgmental. Most men try to avoid women with those traits. If you want to be more successful at dating, you might want to rethink the way you choose to see other people, and you might want to rethink the way you express your opinions about other people.

  12. 42

    Something else in defense of the wedding guy — when I was 20, my best friend married a 31-year-old. She invited her girlfriends and he invited his guy friends. The reception was at her parents’ apartment with a total of maybe 30 guests. It. was. AWKWARD. The bride’s guests sat on one side of the room and the groom’s guests on the other. We tried to talk, dance, have a sing-along, but we had nothing to talk about, didn’t know any of the same songs, same dances, or same music. Eh, it was nothing that a decent dose of alcohol couldn’t fix. By the end of that night, I was happily dancing and making out with a 31-year-old. Naturally, we never saw each other again. What I’m saying is, it isn’t the guy’s fault that he was out of place at that wedding. He tried the best he could. We don’t even know if he wanted to come to that wedding in the first place. Maybe he tried to bow out, but his girlfriend talked him into going with her. Poor guy couldn’t even go hang out with people his age (the bride’s parents etc) because he was there with his gf and therefore had to try and socialize with her friends. Of course he looked creepy to them — he was much older and out of place. Doesn’t mean he actually was creepy.
    @ Lia, thank you, that was very touching. Back to the guy, maybe he likes to think of himself as a clean slate with no past. I know I don’t. My past made me who I am. I made mistakes and learned from them. All I’m saying is that Ava should talk more about the guy’s past with him, especially since he’s the one who brought it up. Does he think getting together with a woman barely out of high school was a mistake, or does he think it was an awesome rejuvenating experience and he’d do it all over again if he could? She doesn’t have to give him the third degree, just get him to a point where he wants to talk about it (sounds like he might be already there).

  13. 43

    Karl R #41
    “Ava stated they met when the ex-wife and got married at the age of 23. She does not mention what age the woman was when they started dating or when they had sex.”
    Ava said, “…the issue is that she was only 18 when they met and he was 34!” I took that to mean that they began dating at that time, not that they hung out as friends for a couple of years first (although possible). My take is that, if you have questions about something in a person’s past, it’s a good idea to ask, and clarify. It’s all part of the information-gathering process of getting to know someone. Other than that, I agree with most everything else you wrote.
    Anita #39
    I’m sorry about what happened to your friend. It sounds like she was not exercising good judgement as a result of happened to her. But still, it was her decision, however flawed by her experience, to date and bring the guy  to the wedding. She could have brought a guy her own age who could have behaved badly too. She could have attended solo (easy at such a small, close ceremony). And a 25-year-old still has a few more years on an 18-year-old.

  14. 44

    The age of consent here is 16 so, to me, while 18 is young it’s nowhere near illegal. To marry at 23  is young but not jawdropping. I’m 15 years older than my boyfriend so can’t cast stones at the age difference.
    And because ny boyfriend is younger I do hang out with people much younger than me, ie his friends. The alternative is to have completely separate social circles, which I don’t agree with.
    Mind you, I have never been judgemental about age, even when I was a teenager which is when people are usually at their most judgemental? If it really means that much to you, break up with him and only date people who meet your criteria re the acceptability of their past.

  15. 45

    And Karl R lays down a logic smackdown again!
    @ Anita #39: what makes the guy an opportunistic p*ssy chaser?  Dating a 25-year old?  What if he was 28?  34?  Where’s the dividing line between “acceptable” and “opportunistic p*ssy chaser”?
    @ marymary #45: I believe it’s said that one of the secrets to aging well is having young friends. 🙂

  16. 46

    Thanks Sparkling Emerald
    Anita #39
    Fair enough. I don’t see any point in discussing this further as I get the impression you will keep adding more details until you are proved right.
    Rose #37
    Well I personally think it’s off-limits to discuss your partner’s dating history unless both parties agree to it amicably. I also think it’s pointless asking probing questions about their past relationships – if a woman started asking me questions about my past of course I’m going to tell her what she wants to hear and paint myself in a great light. Why would I sabotage myself by painting myself in a bad light, even if it’s the truth?
    The savvy dater can assess someone’s character and whether they are shallow and only like hot young babes simply by analyzing their interactions with them – without the need to probe their past. This is a much more subtle and successful approach – that’s what the dating period is for.

  17. 47

    I don’t know if I would want a man to judge me based on my last relationship. I think we all make mistakes in past relationships, some obviously making poorer choices then others. I would think that it’s better to focus on how they are treating you in the now.

    The only thing I would watch out for is real deal breaking behaviour like being a cheater, violence, abuse, stealing, drug use, etc.

  18. 48
    Karmic Equation

    Karl R
    Welcome back. Let’s not restart on the wrong foot. Don’t get hung up on who made the advances or even the age gap. My point was that the 18yo was likely NOT the victim that some women are painting her to be; and by extension, then HE is not the villain those same women are trying to paint HIM to be.
    We agree in principle.

  19. 49

    @ Karl – You quoted me WAY out of context, but I stand by my original statement that there is a creep factor FOR A REASON and even the MOST mature 18-yo’s aren’t as mature as a mentally/emotionally healthy 34-yo. (And for the record, a 15 year old could have been in choir for a decade and had numerous music lessons, etc. That example is apples and oranges.  When I was 15, I knew a lot more about soccer than I did about sex and relationships).
    I know quite a few men in my peer group (late 20s – 30s) who have slept with 18-19 year olds.  I only know one man who actively attempts to date these girls, and it has zero to do with “because they are hot” (they aren’t), but because he has serious self-esteem problems.  In fact, the 19-yo I mentioned above got dumped after 4 or 5 dates with a 25-26 yo for being “in a different place in her life” (and no, he didn’t sleep with her and dump her, either. He refused to go there). This isn’t a forum of people being dramatic.  Gavin de Becker (who is one of the top crime specialists in the US) wrote in his book “Gift of Fear” that men purposely AVOID scenarios like walking too close to women in a dark parking lot, etc, b/c they KNOW it’s creepy and the only two who don’t either (a) are super clueless or (b) have a genuine malicious intent. Don’t quote me out of context, I am not saying anything about this guy is remotely malicious.  This small fact just indicates that, for some reason, he didn’t exercise the same level of judgement that we’d hope from our partner, and I think Ava would’ve been more comfortable if he had said “What was I thinking?” 
    Ava asked “Maybe he’s not the person I think he is?” If enough people on this comment thread who say that they would be alarmed by the “18” thing, then Ava is not in the minority. (Seriously, Evan, do you want your daughter dating a 34-yo when she is EIGHTEEN?  And don’t we all boo the 25-yo teachers who get fired for having sex/relationships with their 18-yo students?)  In fact, Evan, you’ve quoted the statistic about divorce amongst people who get married under 25 for the exact reason that most people under 25 just don’t have a good head on their shoulders.
    It’s not a matter of he is malicious or she was a victim.  It’s a matter of one person (Ava’s bf) should’ve exercised, from a societal standpoint, better judgement and the other, from a societal standpoint, wasn’t at an age where one typically has great experience or foresight.  She isn’t judging him.  She is questioning his judgment, which she should do in a serious conversation and not let it get the best of her.

  20. 50

    I am 31 years old and have been in a relationship for about 3 years with a much older guy. My bf would be called a pussychaser and me a golddigger because of our huge age difference. We don’t care, we are happy. I was worried at first of this label and was concerned what people might say about me dating such an older man. He had been chasing me for close to two years. He told me yes he was older but he was crazy in love with me and I should just give it a try and give him a chance before judging and seeing doom beforehand. I did and am I glad I did. I got to know the real him and decided I wasn’t going to throw the best relationship I have ever had just because of age.  He’s the funniest person I ever met, he is honest, keeps his word, very attentive and loving, writes me throughout the day from work (to this day even after being together for 3 years), remembers all special occasions, and my family loves him. The only time we remember our age difference is when someone points it out, otherwise we are happy together and planning to marry later this year. And before you conclude wrongly, I am not an uneducated jobless woman. I am college educated and running a successful business.
    I am just trying to say don’t judge before you know someone’s story. I would rather be with someone who makes me happy even if he was older than me, than someone my age who is abusive and immature.

  21. 51
    Evan Marc Katz

    Much more reasonable tone, Angie. But maybe this is where my strength lies – in my ability to separate my advice from my feelings. Seems a few others have a harder time with it. My advice is in the original post – we’ve all made mistakes in the past and if he’s a good boyfriend who continues to treat you right then leave the past in the past. My personal opinion? 18-year-olds are children and it’s super-creepy and questionable behavior on the part of a 34-year-old man. No equivocations. But as long as it was consensual and no laws were broken, it is what it is. Not my place to impose my values on everyone else in the world. But it’s really important that you separate your feelings about May-December romances from the possibility that this guy could still be someone’s good husband material.

  22. 52

    @ Karl R 
    🙂 Great to have you back! 
    @ Goldie
    I agree, my past is what has made me who I am and while I am grateful for the lessons learned, and the growth that I have had. I still would not want a boyfriend to look at me and judge me.  Because while I am more at peace with my past there are still areas that are raw for me, still areas where I am vulnerable.  I guess if I was with a guy who judged me for my past I wouldn’t be with him anymore.
    I don’t disagree that they should be able to share things about the past with each other.  However, in my opinion, she has already decided this is a big deal and I don’t think she will get past that even with more discussion unless she can set aside her judgement and if she could do that she wouldn’t have to discuss it.  Of course I could be wrong on that.
    @ marymary said,  “If it really means that much to you, break up with him and only date people who meet your criteria re the acceptability of their past.”
    Yes.  Because none of us can change our past.
    @ Joe #46
    LOL…  Logic smackdown…  LOL…  too true!!!  I was thinking, “Oh, boy here comes the big guns!!”  But I think you said it perfectly!!!!!
    @ Angie # 50
    You said, “ It’s a matter of one person (Ava’s bf) should’ve exercised, from a societal standpoint, better judgement…”  
    Have you, in all your past relationships and past experience, exercised good judgement?  I haven’t.  
    You said, “She is questioning his judgement…” 
    She is questioning his PAST judgement and judging him now for what he did then.  Who is he now.  What is he like now.  What choices is he making in the present.  No matter how you dress it up – She is not questioning his judgement, she is judging his past relationship and is questioning who he is because of it.
    @ js31 # 51
    Thank you for sharing!  Glad that you have found happiness!

  23. 53

    “Rose #37
    Well I personally think it’s off-limits to discuss your partner’s dating history unless both parties agree to it amicably. I also think it’s pointless asking probing questions about their past relationships – if a woman started asking me questions about my past of course I’m going to tell her what she wants to hear and paint myself in a great light. Why would I sabotage myself by painting myself in a bad light, even if it’s the truth?
    The savvy dater can assess someone’s character and whether they are shallow and only like hot young babes simply by analyzing their interactions with them – without the need to probe their past. This is a much more subtle and successful approach – that’s what the dating period is for.”
    I hear what you are saying. I agree that someone does not think one needs to ask probing questions and the watch the behavior over several months though not just a few dates. Also listen carefully watch a mannerisms, watch if actions match words and above all trust your gut!.
    I feel enlightened reading your response. Am learning more all the time. Ty for that.

  24. 54

    Evan says
    “My personal opinion? 18-year-olds are children and it’s super-creepy and questionable behavior on the part of a 34-year-old man.”
    I agree. I feel really creeped out by this. Shudders! Alarm bells go of in my gut.

  25. 55

    Pewter candlestick? Was this Miss Scarlett?

  26. 56

    Karl, “40+” and “almost 50” place the guy in his mid to late 40s somewhere. We were so much younger than he (not really able to judge his age with the 100% accuracy that you require) and he was wearing those black sunglasses, so we couldn’t see how advanced the age lines were. But clearly your expertise doesn’t extend to photography. If everyone in a photo is young and bare-faced and there is one person who is clearly old and wearing large black sunglasses, your eye will go right to the old person in the shades. I’m not talking about your FB photo bomb kind of shot, where this would be funny, I’m talking about classic fine art photography–oversized photos of and for the bride and groom. Maybe you’d have to see it to believe it. It was such a shame. Every time someone would look at them the first question would be “who’s that guy?” And the bride and groom would say miserably, “I don’t know.” It’s not like they’re going to launch into some long tale about how their friend was raped, and she was a little messed up, and she went through this phase where she was dating creeps, and blah blah blah. (I’m happy to launch into that tale, though!)
    The guy was there to get laid with my messed-up friend. I did not let her off the hook–none of us did–but we knew her situation and it was clear that the guy was just some opportunist.
    Karl, you and your wife are married. This was a guy who knew her for about 3 weeks. Common decency, good judgment, and good social skills would dictate that one not intrude on others’ intimate friendships when one is the stranger, even when one is invited to an event. It is their event, not an opportunity for him to advance his social or sexual agenda just because he can. He could have observed from the sidelines and not insinuated himself into conversations and photos where he was not invited to participate. (And for the record, we were not a drinking crowd, so getting wasted together was not an option.) I dare say that his behavior at that wedding was the end of his chances with her, actually.
    Sorry to disappoint you, Karl, but I’ve been in a committed relationship with a lovely fellow 1 1/2 years younger than I am for several years now. He never says his girlfriend is “older” than he is because he doesn’t see any difference in our ages. He actually would not ever get seriously involved with anyone very much younger than he is, despite having been given those opportunities, and simply because these women were so much younger than he and he does’t think it’s right. He says that he has never gone out with a woman who isn’t sweet and kind. He thinks I’m a fascinating person and he likes women who speak their minds. I would say that I’ve been very successful at dating, thank you very much!!

  27. 57

    Final thought, Karl. You said:
    “You’re coming across as uptight, intolerant and judgmental. Most men try to avoid women with those traits.”
    You might consider revising this sentiment in the future to “most people try to avoid other people with those traits.”
    Women don’t like men who are that way, either. Just for the record.

  28. 58
    Sparkling Emerald

    Anita – Why did the bride & groom not invite parents or any family members ? That question has been brought up a few times, and you are strangely silent on the issue.  You have been ranting on and on about this 20 something only event, as if it was some sort of rave for kids fresh out of college.  It is normal to invite parents, grandparents, aunts & uncles to a wedding, so this 40 something year old who had the audacity to wear sunglasses outside should have had someone his age there.  The fact that the bride & groom treated this like some sort of college frat house re-union and not a family affair is more disturbing to me, than  the fact that a middle age man wore sunglasses outdoors and tried to “fit in” at a social event, where fitting in, is what someone is normally expected to do at such an event. He was in a no win situation, invited to a wedding, where unpredicably, no one over the age of 30 was in attendance.  If he skulked around in the background, the snotty bunch of kids there would have damned him for being a wall flower. When he tried to do what is typically expected at what SHOULD have been a family affair,  and “fit in” that group of shallow 20 year olds damned him for that also.  Why didn’t the photographer direct the photo session ?  Why did he not ask the subjects to remove sunglasses.  (I have been at a wedding where the photographer has asked people to remove hats, sunglasses, push their hair back, scoot over here, etc) I have never been to a wedding with a pro photographer where the photographer did not choose who would be in the posed pics.  (OK, now let’s get some of the bride and her mother — oops, she’s not here, so let’s get some of the bride and her sorority sisters . . . next up, the whole college gang, now let’s get some of  the bridesmaids . . . )  If the photographer didn’t know how to organize and shoot the event, you can’t blame the sun glass wearing middle age dude with a penis.  And unless HE was the one who date raped her, i really don’t see what that has to do with the price of tea in China.
    Oh, and a man who dates a woman with the hopes that eventually things will get sexual, OMG !!!!  This is BRAND NEW BREAKING NEWS !  I’m sure he was the only man thinking about sex at the wedding, counting even the groom.

  29. 59

    Something else that might play a part here is how long ago the marriage occurred. Was it a very recent break-up? That might make Ava more concerned than if her boyfriend has been divorced for 10 years, and has put the marriage and the ex-wife well behind him.
    Anita wrote, “…he was wearing those black sunglasses, so we couldn’t see how advanced the age lines were.” But even so “…there is one person who is clearly old.”
    Well, thank heavens he at least had the good sense to hide his crow’s feet! May I just say, people in their forties are not “old’!

  30. 60

    WOW!  This is a horror story of epic proportions!  So this guy was invited to a wedding by the girl he was dating and he accepted… bastard!!  Then he wore sunglasses at an outdoor wedding… Unspeakably rude!!  And he was in the pictures… OMG. And the pictures were TOTALLY ruined… gasp!  On top of that he tried to fit in and make the best of the situation…how awful!!!  Did he also wear dress shoes with no socks?  Because that would just be going too, too far.
    I am surprised someone didn’t call the police.  It was a shame that he got away with such sleazy, disgusting and “barely legal” behavior!!

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