I was friendly with this guy for over a year. I always thought he was really hot, but I assumed he was gay because he's on the effeminate side, and I witnessed him drunkenly kissing boys at bars. However, in November, he corrected me and told me that he was "definitely straight." As soon as he said that, I asked him out. We've been "dating" ever since, hanging out a couple times per week and having sex every two weeks or so — not exactly a whirlwind romance, but our connection is too compelling to let him go.
He says he has a hard time thinking of me as more than a good friend, but he still allows me to plan — and pay for — elaborate dates. Then he dropped a bomb on me last week: He told me he has a crush on another girl and asked me for advice. Oh, and by the way, he's still making out with men on occasion. I'm a 36-year-old woman — aren't I too old for this bullshit?
Also, I feel like I should have my sexuality figured out by now, but I'm constantly confusing myself. I've had sex with a number of gay men, and I've also tried dating women. I find that I'm only attracted to feminine women and effeminate men — what is my deal?
Girlfriend, whether or not your boyfriend is gay is the least of your worries.
Let's review: He makes out with other people, he doesn't pay for dates, he only sexes you every two weeks, and he's asking you for advice about other women. How much more time are you willing to waste on this guy?
As for your "deal" — comedian and queer icon Margaret Cho said in the latest edition of Original Plumbing Magazine that "I'm really attracted to masculinity whether it's in a female-bodied person or a male-bodied person. To me, masculinity is sexually arousing, that's what I'm oriented to..." Have you considered that you might be like Cho, only attracted to femininity? Forget about being attracted to a gender and go with whatever turns you on. Dump your waffling, freeloading boyfriend for a feminine person — male, female or transgender — who can love you back.