She Has a Boyfriend

We're having a Love Letters party May 6. It's a talk with memoirist, novelist, and friend-of-Love-Letters Jen Lancaster. Drinks, snacks, mingling, etc. Let's hang out. Sign up here.

I am a 42-year-old handsome, fit, divorced dad of two children, ages 10 and 5. I have been separated from my ex for about three years. During this time, I have had many dates and experiences with different women. However, nothing has really worked out. I have learned what Gronk said — that "women are crazy."

There is one girl I see often. Every time I see her, I just melt. Her smile, hair, eyes, face, teeth, neck, and body are really pretty. I can tell from her actions that she is kind, honest, fun, and hardworking. I am almost certain she has similar feelings for me, but she has a boyfriend. The little guy on my right shoulder is telling me to just leave this girl alone and find somebody else. The little guy on my left shoulder is saying that in my entire lifetime, I have only met one or two other girls who made me feel this way, and that I should do something about it. What do you think, Meredith? Should I let my dream girl go or should I do something? If so, what?

– Dream Girl

Before we get going, let me say that we do not take love advice from Gronk. I mean, he's not wrong – "sometimes chicks are crazy," but sometimes guys are crazy too. I'd argue that we all get a little crazy when we have strong feelings for someone. You just made a list of your crush's body parts, and it sounded a little crazy. That doesn't mean you're a bad guy or anything. You're just smitten.

I wish you had told us how you know this woman, because your relationship with her should determine how you proceed. If she's an acquaintance – someone you see when you pick up your kids or go to the gym — I'm OK with you telling her how you feel. There's no harm in asking her whether her status has changed. If she tells you that the boyfriend is still around, you'll have your answer and will be able to move on. If she says she's free to date, you can tell her that you'd love to take her out. Just be smart about how you ask. Do it in a public place, during the day. Don't corner her or say too much. Make it clear that you're not trying to make her uncomfortable.

If she's a co-worker or someone who's very much connected to your world, it might not be worth asking the question. Think about worst-case scenarios and how your life will be affected by her response. And no matter what, don't start anything with this woman (notice I said woman, not girl) if it's a cheat. If you really like her, you should wait until she's single before you make a move. That way both of the little guys on your shoulders will be happy.

Readers? Should he ask? Should he wait? Should he move on?

– Meredith