Dear Trojan Horse,
Not sure what your last STD testing experience was like, but mine was pretty terrible. It involved getting on the phone with several receptionists, all of whom are just about the unhappiest people on the planet. (I once saw a show about maximum-security inmates who worked at a chicken-processing plant. Even they were more enthusiastic about their work.) After determining that it would be cheaper to go to the clinic than pay the insurance deductible, I took three trains to an unfamiliar neighborhood and sat in a stifling waiting room that smelled like Newports, rubbing alcohol and Chinese takeout.
The exam was standard, but the follow-up was ridic. I'd only get a phone call if something was wrong, the woman at the front desk explained. Thanks, but the fact that it's 2008 and your office still employs rubber stamps and mimeographs (thanks for the funding, Dubya!) doesn't inspire a lot of trust in your recordkeeping.
The other half of the testing hurdle is psychological. No one wants to think about the possibility, however small, that they could walk out of that office holding a bunch of pamphlets with bad stock photography and "Cheer up, kiddo!" factoids about some incurable (and possibly deadly) disease.
Have a friendly, non-confrontational talk with your boyfriend, in which you re-state your desire for him to get tested. None of this "Are you cheating?" It's emotionally manipulative and proves nothing. If he's the kind of guy who's slimy enough to cheat on you, he's slimy enough not to use condoms, if it'll free him from suspicion. He could have a host of reasons you've never thought about — a germ phobia, early ejaculation. Or he might just be one of those "types." We all know them. The ones who actually pay attention to the flight attendant, even going so far as to read the little pictograph instruction booklet as she's doing the safety dance. The ones who never go to bed without testing the battery on their carbon monoxide detector and roll over their 401k's within a week of seeking new employment.
If that's the case, you might just have to give up. People like that are never going to change. You don't have to look at his pro-condom stance as proof that he's skeevy or untrustworthy.

 

Dear Image Problem,
A joke? What the fuck kind of joke is that? A rabbi, a priest, and a wackjob with boundary issues walk into a bar on the Internet. . .
The only thing you can do now is find the hottest, best picture you can of yourself and send it over in an email begging for understanding. Showing up at his house looking like a completely different person without some sort of warning is ill-advised and unfair.
Make sure your email, one, recognizes the craziness of your behavior and the fact that he might have major doubts about meeting you ("I'm sure you're probably don't want anything to do with me, but I would love to meet you for coffee or a quick drink and show you I'm actually a very nice person," and two, attempts to explain your joke in a manner that's neither too cavalier ("Ha! Ha! Aren't I a stitch!") nor too serious ("Being told I was too ugly to play toxic waste in the Earth Day pageant was really the beginning of my issues regarding my looks. . .")
Do yourself a favor and take what you did seriously. It was not a joke, but rather a deliberate deception. Don't minimize it. I can only tell you how to stop the bleeding and possibly still get a date out of this guy. It'll take some long talks with a friend or shrink to help you better understand why you did what you did.

I have no idea how to approach new people in real life or online. This is especially true for this girl I've discovered on Facebook. I've been wanting to initiate contact with her for a while now. We're both regularly invited to the same indie dance events, but I never attend. I could try making first contact that way, but after doing so I know I could never live with my disgusting self again. It would be too stalkerish. I know I'm decent looking. I'm quite fit too, but none of this helps with my lack of confidence. She's out of my league. She's an artist and I respect her work. It's not the rejection I fear. I seriously don't want to waste her time. — Hermit Crab