HTT, my friend is scaring off my dates!

Dear HTT,

I have a friend (who’s newly married) who seems to get in the way of my dating prospects. For example, a co-worker of hers twice told her that he thought I was cute and she told him (and told me later) that I was too old for him.

More recently, I went out with a group of friends including a guy friend of hers that had previously expressed interest in me. He and I had a great time--dancing and laughing and kissing until the wee hours of the morning. A few days later, my friend calls me and tells me that she went to visit this guy at work and they talked about the weekend. She relayed the information that this guy likes me but he doesn't want a serious relationship right now. I never got the impression that these two were close friends, so I'm surprised at the level of detail she went into. She went on to further discourage me by saying he has many other women interested in him and that I "shouldn't chase men."

I am so angry that she had this conversation with him (not to mention the hurtful comments she made to me). So my question is, do I confront her about getting in the middle? Or do nothing and just beware, since she obviously has personal issues that I can't control? I'm afraid that if there is any possibility that this guy and I might date--now or in the future--she will kill it. (Granted, if this guy decided to communicate through her rather than with me directly, that would be another issue. But that remains to be seen.)

Also, there is a chance I'm going to run into this guy this weekend (without her around). Is there a subtle way I can let him know that I don't want to communicate with him through our mutual friend, but would like to stay in touch?
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Your letter got me riled up. Where does this woman get off telling someone you’re too old? And, what in the world---you shouldn’t “chase men”? What is this, Desperate Housewives? “Man chaser” is to “someone who dates” as “unpatriotic” is to “someone who disagrees with the war.”

Working up a good head of steam wasn’t helping me get any clarity on your problem, though, so I made all kinds of flow charts and decision trees in an attempt to sort this out. They were messy and ultimately not very useful. But amid the chicken scratch, one question kept popping up: How good a friend is this?

I was tempted to answer the question myself with a snippy “not very.” But it’s naive to pretend that even good friends can’t be clueless or hurtful once in a while. And if this woman isn’t a best buddy, she might still be someone with whom you’d like to remain friends on some level.

If so, I think you should confront her. Well “confront” may be too confrontational. Ha. Talk to her. I think the whole guy/dating aspect carries too much charge, so rather than accusing her of manipulating your love life, consider emphasizing how her comments have hurt your feelings. This brings the conversation out of the “man chasing” realm, which she obviously has some sort of issue with, and makes it more personal. Can you do that? Make it less about the guys and more about the friendship?

On the other hand, if you’re so fed up with her that future friendship is out of the cards, if you suspect she’s more malicious than clueless, I’d just let it drop. And try to keep your dating life as separate from her as possible. (Probably not a bad thing to do in either scenario.)

Along those lines, if you run into the guy this weekend, do you really have to be all that subtle about your interest? Now, mind you, I’m not often one to go out on a limb in this kind of situation, unfortunately. But in your case, the risk seems low. You’ve already got pretty strong evidence that he likes you, even if it’s not in a long-term-relationship kind of way at this point. Can you say, “Hey, I’d like to keep in touch. Here’s my email/phone number so you don’t have to go though our mutual friend anymore”?

Let me know how it turns out.

HTT