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I'm a 24-year-old broke gay man. I am extremely poor right now and just out of a long-term relationship. My previous boyfriend wore me out because I was his sole source of financial support. Other than him, my relationship experience is nearly nonexistent, so I'm not really sure about the formal rules of dating.
The problem is with the new guy I'm about to start seeing. He's very generous, and we plan on dating as soon as both our lives settle down. He keeps talking about treating me to expensive vacations and adventures. He assures me he can afford it and is happy to pay my way. Do I accept his generosity and let him treat me to these great adventures? Or will I end up bleeding him dry like my ex did me? For what it's worth, I try to reciprocate with food and other gestures, but it's not cold, hard cash. I've always been taught to pay my way, and I wonder if a poor guy like me has any business dating. What do you think?
—Too Broke 2 Date
Honey, Sugar Daddy hasn't even started paying your bills yet, and you're already sweating it? Talk about taking the lemons life hands you and turning them into a turd sandwich.
What I don't understand is why these things aren't happening already. You're "talking about" spendy getaways and pricey adventures, but you're only in the planning stages of dating? Huh? Does this mean you haven't started having sex yet? You obviously don't have much dating experience, because otherwise you'd already know that a guy can go from "great potential" to I-wouldn't-blow-him-with-Gwyneth-Paltrow's-mouth over the course of one tiny cocktail.
I mean, how many times have I gone on a second date with a guy I was certain would be the next Mr. Judy, only to have him start licking my face when he was supposed to be kissing it (once), or worse, suddenly begin nipping at my jawline like a hungry little ferret (thankfully, also only once)? I hate to sound like a cynical bitch, but I truly hope you haven't started fucking this guy, who is so far too busy to date and just keeps dangling little treats in front of you like a mistletoe cock ring, because he could just be playing you.
Either way, my advice is to wait and see. If you're not fully into him, don't go out with him. You're already very aware that you don't want to be a financial burden, because you've seen how unattractive that can be. So don't be. Continue paying for what you can when you can, but don't go into debt trying to keep up. If he is actually loaded and wants company for a week in the Maldives, why not let him pay? Youth is fleeting, and you're not going to have that smooth, resilient skin (sob!) or that seemingly never-ending supply of boners forever. Maximizing one's good qualities is how anyone gets anywhere. Right now you're hot, young, and poor. In many cases, the first two qualities outweigh the last. This could be one of them. Happy New Year!