Dear Cheryl: I'm gentle, shy, timid, tomboyish, adventurous and cute. My best friend from high school is gay. He always partied on the weekends and invited the girls and the guys. We all hung out together. He taught me self-esteem. If by midsummer to late fall things don't work out with my one true love, then I'm going to marry my gay best friend. There won't be a honeymoon, but he's the Will to my Grace, or rather, the Jack to my Karen. What do you think? — Grace/Karen

Dear Grace/Karen: Before you marry Will/Jack, you'd better set up some ground rules. For instance, what are you going to do about sex? Are you allowed to have lovers? Is he? Can you bring them home? Can he? What about children? Do you want them? Does he? If you both do, will you "make a baby" together? Use a surrogate or a sperm bank? Adopt?

Is he out of the closet? Will you tell your family members he's gay? Will they have a problem with it? Will you have a problem with their disapproval?

What if you fall in love and want to marry? What if he does? Will you be able to part without a lot of angst?

Where will you live? How will you handle finances? Will you have a prenup?

Every marriage has its own set of problems, but a marriage between a straight woman and a gay man has more than most. Just think it through before you make any decision.

And above all else, don't do this to get back at your "one true love," because you've got many! And they're straight.

Dear Cheryl: I'm a 31-year-old former Catholic schoolgirl. I went to school wearing the usual uniform: pleated navy blue skirt, bobby socks with penny loafers and a white blouse that buttoned up to the neck. I was brought up with old-fashioned values.

As a result, I'm still a virgin. Of course I would love to have my first sexual experience with someone I'm in love with, but I'd rather have sex with anyone than go through life never having had sex at all. I feel like if I don't find someone and have sex soon, I may go through life a virgin. The question is who? — I'm Not Desperate, but I'm Close

Dear IMDBIC: First you have to make a decision. Do you want to wait, say, six months or a year or two years or longer to fall in love and have sex? Or have you made up your mind you want to have sex sooner rather than later so you can stop obsessing about it and get on with your life?

In a way it doesn't matter, because the next step is the same in either case. You need to go where the men are, whether you're looking for someone to fall in love with or just someone you're attracted to.

Where's that? Everywhere! Men are working out at gyms, playing in co-ed softball leagues, sitting in coffee shops, volunteering at charities, attending political rallies, etc., etc., etc. The more you put yourself out there, the more you force yourself to smile and say hello and initiate conversations, the better your chances are of meeting a man who falls into the first or second category.

Got a problem? Send it, along with your questions, tales and rants to [email protected]. And check out my e-books, "Dear Cheryl: Advice from Tales from the Front" and "I'll Call You. Not."

Photo credit: at Pixabay