Dear Wendy: “When Should I Tell Dates About My Divorce?”

It’s time again for “Shortcuts.” For every question, I’ll give my advice in two three sentences or less, because sometimes the answer to a person’s question is so obvious and the need to hear it so great, being as clear and frank as possible is simply the best way to go. Today we discuss when and how much to tell new dates about your divorce, taking “no” for an answer, and how to move from the “just friends” category.

I am recently divorced and ready to start dating again. When do you think is a good time to bring up the fact that I’m divorced? There were no kids, but it was not a mutual breakup (basically, my ex had a nervous breakdown and left after six months of marriage). How much information is my date entitled to know? How should I phrase it? I’m not interested in rehashing the whole thing with a perfect stranger, but am otherwise very open about what happened and how I feel about it. — Divorced and Ready to Date

“I’m recently divorced,” and even a vague “Things just didn’t work out,” is sufficient information for early, just-getting-to-know-you dates. When you feel more comfortable with someone and you’ve moved to a stage where you’re sharing more personal details (anywhere from the third or fourth date to a few months down the line), you can be a bit more open. And if you feel like you just really want to talk about your divorce, your ex, and what happened, you should probably find a therapist if you haven’t already.

About two months ago I started talking to ‘Billy.’ I’m crazy about him, and he says he likes me a lot. The catch? Up until four months ago, he was in an eight year relationship (he’s 26). They were engaged for less than a month and she called it off. He said he felt relieved. At this point he’s not (and probably shouldn’t be) looking for a relationship. I am. I’m worried if I keep seeing him I’m going to get my heart broken. I’m getting attached. But my natural instinct in every situation is to call things off. I’m not sure what the right approach is here. At what point do I decide it’s time to move on? I’m not sure I can legitimately see other people while still seeing him the way my feelings are and I find myself getting borderline jealous already. What should I do? — Looking for Love

If someone tells you he isn’t looking for a relationship, BELIEVE HIM. If you’re looking for more, be honest about that and tell him you can’t date someone who isn’t on the same page as you, but if you’re still single when he’s ready to pursue something more serious, you’d love to give it a try then.

I happen to know a intelligent, caring, sensitive, amazing and beautiful woman. We have been friends for years. She knows I have a crush on her, but I’m still in the “just friends” category. Recently, she was talking to a friend of hers about being single and wanting to change this. I walked up to say ‘hi’ (not knowing what the discussion was about) and her friend said, “What about Mikey?” Awkward for her! She replied, “We have been friends too long and that would be weird.” Do you have any hints/suggestions/sure fire ways to get me out of the “just friends” category and over to the “you have a chance” category?? — Friendly Crush

If your friend knows about your crush, doesn’t want to be single anymore, but still isn’t interested in dating you, you need to accept that for whatever reason you simply aren’t her type or aren’t what she’s looking for and there’s nothing you should or could do to change that. It’s time to move on and find someone who is “willing to give you chance.”

My boyfriend and I have been together for a year and a couple months now, but have been friends for about three years. We live an hour apart, and both work and go to college. We only see each other one day a week, and spend that whole day together. Because of my current car conundrum, I’m not able to visit him — he can only visit me — and I live with my parents. We usually go to the movies, go out to eat, just chill around my house, etc., but lately he’s been complaining about being bored (can’t blame him really, I’m pretty bored myself) and so I try and find things for us to do. I set up double dates, suggest we go bowling, go feed the ducks at the park, or go try an eclectic restaurant, etc. Problem is, he doesn’t like to do much. He says he’s bored, but then when I suggest things, he says “meh” and doesn’t want to do them. I’ve suggested that we do some stuff he wants to do, but he has no opinions or ideas in that regard either. When he visits me, he always ends up just texting his friends or complaining about how bored he is. I’ve told him not to worry about coming to see me unless he wants to, and will be open to having a good time. Was that the right thing to do? What should I do? — Bored Too

Sounds like your boyfriend was ready to break up but didn’t have the guts to do it himself. It’s always better to be alone — and be available to someone new and exciting! — than be in a lonely relationship.

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