Wow, who needs enemies when you can provide all that negativity yourself? More importantly, what do you have against Bette Midler? In all seriousness, though, your letter made me do a lot of thinking. On the one hand, it paints you as depressed, hopeless and resigned. On the other hand, you come off as someone healthy enough to accept that we live in a beauty-obsessed culture and that you don't meet the ideals we see everywhere. I think you need to reconcile the conflict of these two stances and find a place you're happy with.

I believe that most people on the net fall somewhere between psycho net murderer and Pamela Lee look-alike; that is, they are pretty average. It is true that the net seems to occupy a space in between total reality and total fantasy, being full of both potential and disappointment. So how do you know if your guy is talking to you because he genuinely enjoys it, or because he thinks you might be a Pamela Lee? You don't know, really, but it doesn't sound like you can be sure that's what he's looking for, either, so how can you justify pulling the plug, especially when you've bonded so much? I'd suggest you level with him. Send a photo, have some fun and tell him that the lighting was bad in the modeling agency that day. He might appreciate your self-deprecating tone, the same way he seems to appreciate your time together in conversation, and he'll definitely appreciate your honesty. He might also surprise you and not be as looks-conscious as you are. Or he might think you're beautiful. I think you owe it to him, and yourself, to find out. Besides, what do you have to lose if the alternative is to end things anyway? Bottom line, you'll only have wasted his time if you bail without giving things a chance. I'm guessing, by the way, that he might have figured out you're self-conscious and probably no Pamela Lee, but he hasn't used that as an excuse to stop communicating all these months.

Whatever you do, you've got to lose some of your baggage and quick, you jaded 23-year old. Simply stating that you've come to terms you're no beauty is a far cry from being ready, willing and able to find a meaningful relationship, and one bad blind date should hardly be a crippling blow. You need to give yourself and others a chance to like you. Most importantly, however, remember that people connect on all levels, and while the physical is one of the strongest, it is by no means the only or most important level, and your friendship with him demonstrates that. We've all got more to offer than our looks. If you sabotage all of your relationships because you decide you're not beautiful enough to be with someone you like, then you've done something that you know is wrong – you've let looks matter too much.

Sincerely,

Mike