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Dear John: Okay To Date Your Ex’s Sibling? Depends On The Sibling

Tuesday, April 15, 2014


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

Dear John,

I broke up once and for all with an on-again off again girlfriend I dated for a couple years. (This was a couple of months ago.) But her younger sister emailed me recently to get together for a drink and a “talk,” and I’m looking forward to it and very anxious about it also. We were pals and we would do stuff together like Christmas shop for her sister and it was fun although there was never a hint of anything at all beyond a sisterly friendship. But we got along great and being a guy, I can’t lie and say I’ve never thought about what it would be like to be with her. (Just so you know, I am 38, my ex is 36 and her sister just turned 30.) So anyway, I got this email from her and I have no idea what it’s about, but I’m thinking it’s the obvious thing and she wants to see if we both might have stronger feelings for each other than we’ve let on. Is this cool, though, as far as her being the sister of my ex-girlfriend? I have mixed feelings about it, and I have some friends who say yes and some who say definitely not. My ex used to drive me crazy (and I did to her), but I really don’t have any desire to humiliate her or hurt her or anything like that. But I’m almost 40, I want a family, and I don’t feel like I can rule anything out when I already know I get along well with this person, you know?


On The Fence

Dear On The Fence,

The situation you’re describing could work, or it could be an epic disaster. Which one it is depends entirely on the people involved – what their motives are, what their relationship is like, and what kind of people they are. There’s not nearly enough information in your letter for me to know any of that, so I’ll give you my perspective, but it’s up to you to decide what to do with it.

The positive scenario is that your ex’s sister is genuinely attracted to you and regrets the fact that she knows you only because you dated her sister, but she understands life can me messy sometimes. Before contacting you, she would have talked to her sister about what she was planning, if not to get her blessing, then to at least prevent her from being completely blindsided by it. She would have assured her that this is something that she only began thinking about after the two of you broke up. And she would have really listened to your sister’s response.

At the other end of the spectrum is the possibility that this isn’t about you at all, and you simply represent an irresistible opportunity to express the anger and resentment the younger sister has been harboring toward your ex for years. You may not want to hurt or humiliate your ex-girlfriend, but that may be exactly what her sister wants to do.

So which is it? Obviously, I have no way of knowing that. If you sincerely believe the former description applies, then I don’t think dating your ex’s sister is wrong, but you should be aware that even under the best circumstances, there are bound to be uncomfortable (or worse) moments with relatives, mutual friends, etc. It would be a difficult situation, especially at the beginning. There’s no getting around that.

If there’s even a chance it could be the latter scenario, though, then the answer is obvious: dating her would be a terrible mistake.

One last thing to note is that you do sound like you’re getting a little bit ahead of yourself. All she has said is she wants to get together for a drink and a talk, right? This may be what you think it is. But I’d let her go first.

Dear John,

My wife’s best friend from college and her husband are coming east and want to know if they can stay with us a few days. Neither one of us wants that to happen because when they were here last two years ago, the husband (well, all of us) had too much to drink one night and made a pass at my wife. He did it when no one else was around and my wife didn’t tell me about it until after they left. She was more amused by it than embarrassed. You couldn’t come up with a person my wife would be less likely to be attracted to than her friend’s husband. What I mean is that this wasn’t a big deal for my wife and me, it was more of a joke, but we still don’t want him staying here on his next trip to town. My attitude is, we open up our house to you and that’s how you treat us? Okay, that won’t happen again. My question is do we make up some excuse to give my wife’s friend, or do we tell her the truth? Part of me hates the thought of making up a convincing lie that prevents them from staying with us but still lets my wife and her friend see each other, having to remember not to say anything to give away the lie, etc. Why should we have to do all that? Easier to say in so many words you can’t stay here because your husband’s a jerk. Even though he did what he did, though, I don’t want to put any stress on her marriage. For all I know, that was the only time he ever did anything like that. What do you think? Lie, or truth and consequences?


Unwilling Hosts

Dear Unwilling Hosts,

I wouldn’t worry too much about devising a convoluted explanation for why they can’t stay with you. Your wife should just say something like, “Ooh, the 15 th? That’s not really a great time for you to stay with us. We’ll be around, though, and I’d love to have an opportunity to see you. Let’s get something on the calendar.” That should be the end of the discussion. If your wife’s friend presses her for an explanation, though, I don’t think there’s anything wrong with being honest about what happened. Drunk or not, this guy did what he did; it’s not up to you to cover for him or to determine how big an issue it is in their marriage.

Dear John,

Quick, simple question: I’ve started dating a guy and he’s a super guy, funny, emotionally and financially stable, considerate, even handsome…except for the fact that he’s just too too hairy! At the risk of TMI, when we’re intimate, half the time I feel like I’m petting him! He doesn’t seem the least bit self-conscious about it and he seems very comfortable with himself, so I don’t know how to raise the issue of hair removal or even if I’m right to do so. I would hate to hurt his feelings or make him self-conscious and isn’t self-acceptance and not buying into our looks obsessed culture a GOOD thing? Maybe I’m the one who has to change…I’m open to that, too…but one of us does, because all I know now is that when he’s undressed it’s all I can notice or think about. What should I do??


Hair There & Everywhere

Dear Hair There & Everywhere,

I agree with you that his comfort with his body is commendable, but I don’t think you’re shallow or superficial for wishing he were a little more meticulously groomed. I’m sure a lot of women – most even – would feel the same way. And I think most men would want to know what they could do to make themselves more attractive to their girlfriend, assuming their girlfriend’s expectations were reasonable. Whether you’ll hurt his feelings depends on how you present your question – and it is a question, not a request. Tell him you’re curious how he would look if he were a little less hirsute, and ask him if he would consider trying some type of temporary hair removal. Tell him about his options if he doesn’t already know what they are (probably not, judging from your description), and let him know that if he doesn’t like the results, it will all grow back (although the implications of that for your relationship are a subject for another letter). Keep it light, be supportive, and I think there’s a good chance he’ll give it a shot and like the results – especially if he knows you like them.

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] . He's away from the advice desk this week, so he's chosen some of his favorite letters from previous columns to share.


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