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Don't hurt this guy twice

Dear Carolyn: There's this guy I always thought was cute, but he had a girlfriend. In the last few months, though, we both became single, started flirting, then dated. It was a lot of fun; there was great chemistry, we have a lot of interests in common, and he is very into me, relationship-oriented, available and sweet.

But a few weeks in I started getting uncomfortable and ended it. A lot of our conversations were devolving into his expressing his insecurities, and my either reassuring him or expressing my own fears in order to somehow level the playing field. His long-term relationship was a painful one, in which he felt like a victim of his partner's ups and downs. I think he's been a part of a lot of insecurity-based interpersonal drama in the past.

So I told him I didn't think the time was right for us. He was disappointed but took it well. Since then, we've been in casual contact as friends.

I've been on a number of dates with guys I met online since then, but none seems as enthusiastic about me or as compatible. Do you think there's a way I can embrace or at least accept this guy's sensitive side, or does it sound like a big liability? I myself am not always the totally secure, confident individual I imagine myself dating. I don't want to jerk him around or give him false hope, but I also don't want to dismiss him if he's just a diamond in the rough.

-- Anonymous

A. Can't it just be that he needs more than "a few months" to get over his ex? (Face rub.)

To answer your question: When you're not sure about making a certain choice, it's helpful to imagine it in the bluntest possible words.

Such as: "I dumped him because his drama got on my nerves, but several failed dates have me thinking he might be the best I can do (better than I initially thought, better than nothing?) and he's cute enough for me to rationalize it."

If you think that's accurate, then you know what to do with this diamond-in-the-rough idea.

If that's not accurate, then you need to make a 100 percent desperation-free accounting of what, exactly, makes him a just-right-for-you diamond, now, as-is. Anything less than that is teeing up to whack him twice.

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Avoid temptation

Dear Carolyn: I live abroad, in a city that is well-known for its nightlife and narcotics. My husband was deeply involved in that scene "back home"; part of why we moved away was to give him a chance to start over. He's made a sincere effort to change and has made some progress, but it's a long, complicated process.

Now, an "old friend" of ours (more of an acquaintance) is thinking of coming here on her globe-trotting journey, and I have no doubt the "nightlife and narcotics" are a major attraction for her.

Do we offer her a place to stay, or do we avoid temptation and have her stay somewhere else? I worry that if she were to stay here, she'd drag him into some sort of trouble, but I know I can't build walls around my husband and he has to learn self-control. If it matters, she was more my acquaintance than his, so it's really up to me to respond.

-- An Expat in Party Town

A: For your husband's fresh start, you moved to Ibiza?

Tell your friend you and your husband are trying to break away from the club scene; no need to single him out. Then, say you're asking would-be houseguests to stay in hotels, to minimize temptation; you hope she understands. TMI? Maybe. But there's no shame in being tempted or in fighting it, so who cares if this acquaintance knows?

And while you're right that you can't isolate your husband, it's also just common sense to avoid obvious temptations until he's at the sturdier end of this "long, complicated process." As you know, there are few temptations more powerful than someone who rationalizes the behavior you're trying to leave behind.