A light crush letter today, and maybe some adultery tomorrow ...
I need some help. I have been friends with a guy for about five months now. We have a lot in common and he is everything I want in a boyfriend. I am very afraid that I am now trapped in the dreaded friend zone and I don't know what to do. I have liked this guy more than friends from the beginning, but I think I was so afraid of screwing up that I haven't tried to hook up with him or even shown him that I like him more than a friend.
We have been talking a lot lately, and I have met most of his friends and his mom. But ... he recently asked out my best friend when he was drunk. It isn't like he is asking me to set him up with my friends or anything like that, but it caught me off guard. Of course she said no, because she knows how I feel and she thought it was really sketchy of him to pursue her. I thought it might be clear that I like him more than friends, but should I tell him how I feel straight out? And if so, what should I say so that I don't freak him out and send him running? I am also afraid of messing up our friendship and making things awkward.
– Ms. Friendzone, Boston
You're afraid of making things awkward? Trust me, Ms. Friendzone, you're already living on Planet Awkward. You've been into him for months, and he's drunkenly pursuing your best friend. I don't know what you think you're trying to preserve here.
You must be a grownup and tell him how you feel. Go for extreme clarity. Try: "Hey, I need you to know that I've had romantic feelings for you from the start of our friendship. I want to pursue this and I hope you do too. How do you feel about me?"
If he starts running, at least you have an answer. If he's wishy-washy about it or just wants to be friends, you can do some soul searching about whether you really want him around.
The longer you wait, the weirder this gets. Please tell him the next time you see him (maybe tonight?). And try to keep the evening to a one-drink minimum so that you don't have to question your delivery or his response.
No one has ever written me to say that they regret disclosing their romantic feelings to a crush. They only write in when they regret not saying something sooner.
Readers? Is there a friendship to preserve? Is his hitting on her friend a deal-breaker? Does he know how she feels? What should she say? Help.