I'm a woman. For some reason I keep ending up dating men who are just discovering that they are gay. Is there any way I can ask a question about someone's sexuality without being insulting?
The short answer to your question is yes, and no. While your intent when inquiring about another person's sexual orientation may be well-meaning and self-protective, the object of your affection may get bent out of shape no matter how you go about gathering information. And, asking doesn't always yield an honest answer. Coming out to one's self and others is a complicated, difficult, and sometimes frightening process for many people who identify as gay, lesbian, bi, queer, or something other than "straight." A person who has yet to come out to her- or himself can hardly be expected to come out to you over a dinner date! That said, your desire to pursue a partner who is interested in pursuing you is completely reasonable, even though you may need to tread sensitively during conversations with dates about their sexuality.
One possible way to avoid needing to broach the sexuality subject on a date is to sharpen your intuition. Spending time with gay people, reading a gay novel, or seeing a gay-themed movie won't give you magical "gay-dar" powers, but, at a minimum, these activities might give you some information that could heighten your awareness and make future dates less awkward. Another less-than-direct tactic would be to tell your current beau about your past experiences with nascent gay men, and express your hope that you are just as good at attracting straight men. This may be the hint your date needs, either to reassure you of his mutual attraction, or to alert you that he's not interested in being your main squeeze. Of course, there is also the direct route. Something like, "I think you're cool and I'd like to date and get to know you better, but I'm loath to make assumptions about people. Do you date women?"
If and when you decide to scout out the sexual ID of your next date, let "unassuming" and "non-hostile" be the guides for the words you choose. Remember, no one is obligated to share their sexual orientation or other personal information with you. Helping someone to feel comfortable in your presence may go a long way toward open exchanges of feelings, thoughts, and attractions. For more information about sexuality and sexual orientation, check out Should I explore my sexuality? and Fantasizing in the wrong direction? in the Go Ask Alice! archives.
Turn the tables for a moment and consider that there may be a straight guy out there experiencing your very predicament, who is also wondering how to determine whether the women he dates like him, or like, like him. If you were on a date with this guy, how would you prefer to be asked about your sexual orientation? Directly? Indirectly? Not at all? There is no right answer, but treating others as you would like to be treated is a good guide.
A final thought here: you sound like a caring and compassionate person, so perhaps you attract some men who are questioning their sexuality and in need of a good friend. Could your kind nature be helping them out of the closet? "Yes" would not be such a bad answer, and it just might better your chance of someday meeting an even better Mr. Right.Alice!