He's Leaving and I'm Too Insecure to Give Him My Number

Dear Mona,

I like this boy. Of course I can't know if he is gay or not, because we are total strangers. I see him 3 days a week during class. After exams he is going to a new school and I’ll never see him again. I am thinking of various ways to approaching him mostly anonymous, like following him to his house to see where he lives or slipping an anonymous letter with my email address or mobile phone number in his bag. I haven't done anything yet, but time is running short and I don't know what to do! I'm really crazy for this guy!

PS: I'm a very shy and insecure, so I don't think I will have the courage to confront him directly.

Dear Desperate Diva,

Crushes come and go, but restraining orders are forever. Don’t stalk the guy or slip him an anonymous note. You don’t even know if he’s gay or if you’ll even like him, for that matter. You only “think” you’ll like him. The jury is still out on that one. I can say this with confidence because I, myself, have had many pain-wrenching fantasies destroyed the moment my crushes opened their mouths.

Here’s the deal: I know you’re shy and insecure, but you’ve got to give it your all if you want to get to know the guy. Time is ticking and the direct approach works best. I’m not a fan of sneaking around and I would never suggest my readers find the loophole in their self-contracted insecurities. It’s not worth it, especially since you don’t even know if the guy is gay.

If he’s leaving your area, you’ve got to act fact. This means you have to find the courage to say hi. Sneaking around and being indirect can end in disaster and there still is no guarantee you’ll see him again.

Jumping over a hurdle of insecurities is tough; I know. I’m not suggesting you walk up to him and say, “Hey, I’m gay!” What I do suggest is starting a conversation with him, asking him if he wants to hang out, and being his friend. Tell him you want to keep in touch after he leaves school. Then offer him your email and mobile. That way you can get to know the real guy not the fantasy in your head.

We are not born with courage, we develop it over time. You have yet to believe in the courage I know you have because it has yet to be tested like this. This is your opportunity to get out of your shell and take a chance. Even if you don’t get this guy, you’ll have less nerves when you strike up a conversation with the next one.

Yours on a limp,
Mona