Dear John: Will His Old Man Be Hers Too?

Tuesday, June 19, 2012

John Simpson, GoLocalProv Advice Columnist

What’s your problem? Write to John at [email protected].

Dear John,
 
I’m in my mid 50s and my son is in his mid 30s. We see each other a lot, but we’re not real close. I’ve been divorced from his mother since he was a teenager and I don’t think he’s ever stopped being mad at me for leaving. Long story. Anyway, he was dating a woman that I had a chance to meet at a couple of family functions, but I don’t think it was too serious between the two of them and I have come to find out that they’re not seeing each other any more. I’m not with anyone either, and truth be told, I rarely meet anyone I’m interested in. I got to know this lady pretty well the couple of times I saw her, though, and we just seemed to hit it off. So I’m thinking of asking her out. She was about midway in age between my son and me, so it’s not like there’s a big age difference there. I mentioned this to a buddy of mine, though, and he thought it was a bad idea, which to be honest, I didn’t expect. So now I’m wondering if he’s right and figured it couldn’t hurt to ask your opinion. Thank you.
 
Sincerely,
All’s Fair?

Dear All’s Fair?,
 
I agree with your friend. It sounds like a bad idea. There’s nothing technically wrong with it, you’re all adults, etc., but there’s something about it that just doesn’t sit right. And emotionally, there’s too much going on here for you to be so blasé about dating your son’s ex-girlfriend, however unserious their relationship was. Your son already resents you for leaving when he was a teenager. You imply there’s a lot of back story there, but you don’t provide any. You simply suggest that of all the women you could date – people you’ve met through your job, people you know from church or social groups, friends of friends, and so on – of all the women you could date, the only one you’re interested in just happens to have recently broken up with your son. Really? There may be nothing at all to this – no psychological subtext, no intergenerational rivalry, no weird power games. But I wouldn’t bet on it, myself. Find your own girlfriends. Stay away from your son’s, whether there’s an “ex-“ in front of them or not.
 
 
Dear John,
 
I have a transgendered friend. She goes out a lot with guys she meets through popular online dating sites. But nothing in her profile indicates she’s transgendered, nor does she tell the guys that she dates. (I know because I asked her.) We recently got into a little bit of a debate about this – I feel she’s not being honest about herself and that these guys would want to know. Wouldn’t you? She disagreed and got quite upset about the discussion. Was I wrong to bring it up?
 
Signed,
Values Honesty

Dear Values Honesty,
 
How is this even any of your business? You say you value honesty, but I bet she would value a friend who was supportive and who didn’t monitor her dates and find problems where there are none. If she wants my opinion, tell her to write. As for you, stay out of it.
 
 
Dear John,
 
I just broke up with a great girl, again, and it’s always the same. I fall in love with a girl, I do everything I can to win her over, then when I do, I lose interest. The same person I couldn’t live without is someone I’m through with six months later. Why do I do this? I used to think when I found the right person, it would last forever, but now I’m starting to get scared that this is just how I am. How do I fall in love and stay there?
 
Sincerely,
Short-Lived Love

Dear Short-Lived Love,
 
It’s easier for me to speculate why you do this than to offer you a way to stop doing it. I think you’re probably deeply insecure about your desirability as a boyfriend, so you pursue these women not because you’re truly interested in them (despite telling yourself that you’re “in love” with them) but simply to see if they will be interested in you. Once they are, you have your answer, so there’s really no reason to stay together and you quickly lose interest. Your relationships don’t last because that was never their purpose. On some level, the entire point of your pursuit is simply to see if someone you find sexually attractive will reciprocate. The unfortunate thing is, when someone confirms that yes, you are desirable, that doesn’t assuage your doubt that you’re not. You need that same assurance from someone new to prove the last one wasn’t a fluke. So the cycle repeats. You don’t give us any indication of your age, but if you’re still young, this may be part of the process by which you’ll reach emotional maturity. If this has been going on for two or three decades, though, you probably need more help than I can offer you through an advice column.

John is a middle-aged family man from Providence, Rhode Island. If you learn from your mistakes, he’s brilliant. Write to him at [email protected].

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