Avoiding the friend zone

Updates coming tomorrow ...


I'm hoping you and your readers can help me out. I was introduced to this girl, let's call her Emily, several months ago through one of my good friends, but not in an effort to set us up. What I've come to realize is that I like this girl. There is of course a complication -- I've suspected that she was dating someone else, "Jim."

Emily met Jim when they were freshman in college and they dated a while. Jim went abroad, and while he was gone, he and Emily broke up because she met someone else. She and that guy ended their relationship earlier this year. Everyone is now graduated and Emily and Jim have been spending a decent amount of time together. According to my friend, they started officially dating again two days ago.

The friend who introduced us has suggested that I tell Emily how I feel anyway. So now I need to decide whether I say anything to Emily about how I feel and let her know that there is someone other than Jim out there -- or say nothing.

Worth mentioning is that Jim is a jerk to people quite often, especially to Emily, and other people beside me notice this as well.

Part of me wants to tell her now because I have a habit of becoming friends with girls I like and getting stuck in the friend zone and I don't want this to happen with Emily. But another part of me says sit back and see what happens. I'm just tired of being too cautious around people and missing out on something good, but don't want to screw up by doing something stupid. Please help.

– Looking for Some Guidance, Western Mass.

This would be a complicated mess if Jim was your close friend, LFSG. But he isn't, right? He's just the friend of a friend, and no one seems to like him very much. You don't have to worry about losing him, which makes this rather easy.

Tell her. Be brave. Explain that you've developed a crush on her and that you were bummed to hear that she's dating her college boyfriend. Then give her space. I have no idea how she'll respond, but at the end of the day you're doing this for you. You're letting the world know that you don't want to "sit back and see what happens."

For the record, I don't advocate hitting on other people's girlfriends, but this is more about staying honest. You're just letting everyone know how you feel.

The only risk here is that you might lose Emily. If she doesn't reciprocate and wants her life to be simple, she might keep her distance from you after your disclosure. But that's OK. She's not your close friend. You know what zone you're shooting for.

Readers? Is it OK for him to tell Emily how he feels? What is his friend's role in this? Thoughts about Emily and Jim? How can he stay out of the friend zone? Help.

– Meredith