Originally published March 17, 2005:

I'm 19 and closeted. I've been chatting with a guy on the Internet for six months and now he wants to meet. I'm convinced that he's too good for me. Aside from looks, he's out and older and I don't know why he'd want to be with someone like me. My other online friends—they're the only people I'm out to—think we should meet. I'm effing scared. I'm not going to ask you to compare our pics, but is there a concrete checklist to verify if someone is out of your league?

Insecure In Internetland

My response after the jump...

The good news: If you meet this boy and he's into you, III, then you're in his league. That's because each and every one of us gets to decide who plays in our own personal league. If he invites you to play, you're in.

Now the bad news: There's lots of scum floating around on the Internet—this applies to you too, DAD—and you have to be careful. While this may simply be a case of your own insecurities preventing you from recognizing whatever it is about you that this other guy finds attractive, something more sinister could be going on. You say you don't know why someone better looking, older, and more experienced would want to meet you. Unfortunately in some cases it's because younger, closeted, and insecure guys are easier to manipulate. So this guy is either honestly into you or he's an asshole looking to take advantage of your youth and inexperience. If you decide to meet him, III, meet in a public place, tell someone where you're going, and watch out for red flags. Does he pressure you? Does he try to get you to do things, sexual or otherwise, that make you uncomfortable? If so, run like effing hell.