Katie-Ann from Atlanta, GA asks:
I’m 30 and I’m still a virgin. For a long time I was waiting until marriage and then for a longer time I was waiting for the one. And now finally, I just want to get rid of the “virgin” label but since I’ve waited so long…the men I meet don’t want that particular burden. I feel stuck and I’m scared to death life is passing me by. What do I do?
I’m pretty sure your hymen isn’t intact after 30 years—so no need to put the ghost of it on the table when you’re getting to know these men. I mean it’s really none of their business. And when you finally get down to the act, just deflect any remarks about your “tightness” with dirty talk. So if he says, “Wow you’re so tight” just say, “Yeah, you like that huh?”
And it will happen for you. The magic of being a woman is that you can definitely get laid if you want to get laid. So stop overthinking it.
Keep going out. Keep meeting men. And let yourself date and get to know these men without making it a thing.
And then let one of them take you to bed.
Fair warning though: After all this buildup, you’re going to be bitterly disappointed no matter the man or the connection. Because having sex for the first time, regardless if you're 16 or 36, is going to be awkward and uncomfortable even if you’re the only one in that bed that knows you’re a virgin.
Janet from Brooklyn, NY asks:
Why do men like to send unsolicited dick pics? What am I supposed to do with it?
I’m pretty sure that’s chain mail and you’re supposed to send it to 10 of your closest friends or else suffer the wrath of God.
And I know they say don’t blame the victim but I wonder what you’re doing to make these men think you’d even want a picture of an unemployed, out of work penis—just hanging out by itself, not doing anything at all. That’s not even a porn category and everything’s a porn category.
Indira from Chicago, IL asks:
I don’t know if you believe in that stuff or not but as someone back out on the dating scene, what do you think are the three signs I should avoid? Yes, astrological signs.
Just three? That’s easy.
Geminis, Scorpios and Leos.
All day. Everyday.
Cross the street. Close your legs. Turn your back.
And this is going to be hardest to do when faced with the Gemini charm. And boy is he charming.
And unapologetically shiftless but even that’s charming too (in the beginning).
He’ll charm you right unto your back but the whole time leading up to it you didn’t even think he wanted sex because it was all jokes and laughs and surface topics.
He never even came on to you but now you’re naked and he’s holding your arms above your head so you have no control over the depth of his thrusts.
And then the next day it’s back to jokes and laughs and surface topics.
And that’s the seduction.
And you spend the next year trying to figure out if he feels anything for you.
Except they’re all androids and feelings are sold separately.
And then you run. Right into the arms of a Scorpio.
And find yourself thinking. Finally! A man with depth!
But he’s not. He’s just an accountant. They’re all accountants—meticulously tallying every word and deed in a credit and debit column. Marking down every slight in pen and every effort in pencil.
And then you stay longer than you wanted to because of the passionate fights (about the bookkeeping). But when you finally leave, thinking, it can’t get worse.
You meet a Leo.
Beautiful. Beautiful Leo.
And you spend the whole relationship holding a mirror in front of your face so that he can always look upon the one he loves the most.
And as your arm tires and your soul grows parched.
Because this is who finally breaks your spirit and makes you contemplate White men.
So I say, stay away from them all.
Jemal from Baltimore, MD asks:
Who do you think takes the biggest L’s on television?
L’s as in, they never get the W or the girl or the promotion or the accident free vacation? Just off the top of my head, I’d say:
Hazel-E (Love & Hip Hop Hollywood)
Meg Griffin (Family Guy)
Millhouse (The Simpsons)