Q I'm a 31-year-old straight woman. I have a good job, great friends and average attractiveness. I've dated close to 30 men at this point, and I can't wrap my head around this: I've never had a boyfriend or dated anyone for more than a couple months. It's really starting to wear on my self-esteem. I don't believe anything is wrong with me, but the more time goes on, the more I think I have to be doing something wrong. The guys ghost me or things fizzle out or we're not at the same point in our lives. This is particularly true for one guy I've remained friends with (common social circle) who is struggling with his career, though things are still awkward because it's clear there's still something there.
Another area of concern: I'm still a virgin. Catholic guilt resulted in me being a late bloomer. Once I got more into dating, my low self-esteem coupled with the fact that I've basically decided I want to be in a monogamous committed relationship with a guy before having sex, relationships just never happened. I don't have unrealistic expectations that I'll marry the first dick that sticks itself into me—but I've waited this long, so I'm not going to jump into the sack with just anyone without knowing that I can at least trust them. The only guy I really do trust is Somewhat Depressed Guy, but propositioning him could further complicate our friendship. Is something wrong with me, and what should I do? —What's Wrong With Me?
A I get variations on the first half of your question—is something wrong with me?—all the time. But it's not a question I'm in a position to answer, WWWM, as I would need to depose a random sampling of the guys you've dated, interrogate your friends and grill you under a bare lightbulb for a few days to figure out what's wrong with you.
And you know what? Nothing could be wrong with you. You may have pulled the short straw 30 times in a row, and you just need to keep getting out there and eventually you'll pull a guy who won't ghost or fizzle.
As for the second half of your question: What the hell should you do? What you've been doing hasn't worked, WWWM, so maybe it's time to do something else. Like fuck some dude on the first date. Or if that's too drastic, fuck some dude on the second date. Or better yet, go to Somewhat Depressed Guy and say: "I don't think you want a relationship right now, and I'm not sure I do either. But I like you and trust you, and I could really use your help with something."
While the commitment-and-monogamy-first approach has worked for some, WWWM, it hasn't worked for you. And being a virgin at 31 isn't boosting your self-esteem. There are lots of people who jumped in the sack and did a little dick-sticking with people they barely knew but had a good feeling about. The jumping/sticking/dicking approach doesn't always lead to committed and/or monogamous relationships, but it can and it has and it does.
Somewhat Depressed Guy might be somewhat less depressed if he was getting some, you might have higher self-esteem if you finally got some, and dispensing with your virginity might make dating after you part ways seem a lot less fraught.
Q I'm a virgin in my late 20s. I'm not waiting until marriage, just for the right person. I've dated enough and had enough fun to continue being a happy, normal, socially competent guy, much to the disbelief of my various knuckle-dragging, vagina-blinded pals. I've been dating this gal for a few months. She's special—we have tons of chemistry and she cares about me.
We had a brief conversation about my lack of experience when we first started dating, and she was very cool about it. I really like this girl, but I'm not sure yet if she's the future Mrs. I am a worrier (thanks, mom!), and I find myself thinking that if I share this with her and somewhere down the road we end up breaking up, she's going to be even more devastated because I shared my first time with her. Am I just having silly virgin worries? Not only am I concerned about her feelings if things don't work out, but I'm also concerned that I might become vagina-blinded—that I might immediately tell this girl I want to spend my life with her just because she's having sex with me only to find myself a few years down the road feeling trapped. What should I do? —Very Indecisive, Really Gettin' Naughty
A You should fuck this girl—provided, of course, that this girl wants to fuck you.
You could wind up saying things you come to regret or have to walk back—her vagina might be that bedazzling—but that's an unavoidable risk, and not one that's unique to virgins. The right vagina, ass, face, skill set or bank balance can blind a fucker with decades of experience. The only way to avoid vagina-blindness—or ass-blindness, etc.—is to never have sex with anyone. And I don't think you're interested in celibacy, so stop freaking out about the risk that you'll imprint, duckling-like, on the first vagina your pee-pee sees the inside of.
Q I've been with my boyfriend for more than a year. He's the first person I've had sex with. Four times now while we were having passionate sex, he has slipped out of my vagina and accidentally penetrated me anally. That shit hurts, and I can't help but cry. I know he feels super guilty each time. We've engaged in a little anal play before, and I wasn't really a fan. But I'm not adverse to the idea of using a butt plug. Do you think this would work? —Wrong Hole, Anal Torment
A My own personal sexperience with anal led me to doubt claims of accidental anal penetration, WHAT, as anal penetration always required focus, precision and proper breathing techniques—in my own sexperience. But listeners of the Savage Lovecast schooled me in Episode 340, and I'm now convinced that accidental anal penetration is something too many women have experienced.
A strategically deployed butt plug sounds like an excellent solution to the problem, WHAT, but get yourself a plug with a wider-than-usual base to prevent your boyfriend's misdirected cock from pushing the plug, base and all, all the way in you (ouch) or his misdirected cock from sliding in alongside it. a