Dear Di,
I have a huge crush on my roommate. He’s sexy, funny, smart, and we have the same taste in music and television. One problem though: He’s straight. I’m just so crazy about him and I think we would be such a good couple if he would just give me a chance. Do you think there’s any point in pursuing this, Di?
—Gay Guy Wants the Straight Guy
Dear GGWSG,
What a tricky situation. On one hand, your roommate may surprise you by interrupting your confession and tearing off all of your clothes in a fit of passion and lust; however, the news could also make him extremely uncomfortable. Should he find your declaration of love to be disconcerting, your living arrangement will likely become awkward at best and unbearable at worst.
You say your roommate is straight. Has he told you this outright? Or has he done or said anything that makes you think otherwise? If so, flirt a little. Invite him to get dinner or watch a movie with you and gauge his reaction. Ask trusted mutual friends if they think this boy could ever bat for both teams. Send out some feelers, but bear in mind he may not be bicurious in the slightest. Sexuality certainly isn’t a black and white subject, but if your Romeo has a monthly subscription to Maxim and can’t stop drooling over the ladies next door, it’s probably time to cut your losses and venture off to gayer pastures.
All relationships require a little risk-taking. No one would ever get any penis or pussy without putting themselves out there. I encourage you to investigate the situation, but tread very, very carefully. Best of luck.
Love,
Di
Dear Di,
I’m attending a wedding in a few weeks and it’s going to be awkward because I’ve slept with half of the groomsmen. I’ve gotten texts from all of the guys hinting they’re hoping to hook up after the wedding. I definitely want to have sex with one of them, but I don’t know who to pick or how to keep the whole situation from blowing up in my face. What should I do?
—So Many Groomsmen, So Little Time
Dear SMGSLT,
Lucky girl! Admittedly, your situation is slightly awkward, but also extremely enviable. Watching two people vow to never sleep with anybody else for the rest of their lives always gets me in the mood to celebrate my single status by sexing up a stud. You’ve got your pick of men and that’s something to be happy about!
You do have some decisions to make, but don’t worry, they aren’t of the rocket science variety. Pick the groomsman you’re most attracted to or the one who made you clutch the sheets and scream, “I do! I do! I do!” Text the others and tell them thanks, but no thanks. Problem solved! And if you’re really worried things will get too complicated, why not bring a down-to-fuck date to the wedding?
If you play your cards right, you’ll be basking in the glow of post-nuptial nookie in no time at all.
Love,
Di
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