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Q: I’m 21 and still a virgin. I also have depression. I’m not bad-looking. I work out and generally keep people laughing. I got a lot of female attention in school, but I was hopeless and still am. Most of my friends have girlfriends, so I don’t understand why I haven’t had a girlfriend since I was 10. I feel myself becoming increasingly violent, to the extent that I have tried to provoke a fight that wasn’t necessary, and I try to intimidate other guys when I’m out. I’ve been unemployed for three years since dropping out of college, and I haven’t really met a girl I was interested in since school. I’ve never made the first move with girls. I never feel compelled to, regardless of how attractive I find them. I do get a lot of eye contact from girls, and I’ve been approached by girls, but we barely ever get past exchanging names before they wander off or their friends pull them away. Writing this out has made me realize I should start approaching girls, but I don’t think it’s just that. Surely I should’ve met someone by now? Any advice would be greatly appreciated. —Hopeless Over Painful Experience
A: Women typically expect the guy to do the approaching, asking out and hitting on, HOPE, so that’s definitely something you’ll have to work on. And if a woman is making eye contact with you in a space where it’s generally understood that people are open to meeting new people, flirting with them, and potentially fucking them (house parties, bars, clubs, CPAC), eye contact is an invitation to introduce yourself.
But if women are approaching you and then “wandering off” after conversing with you for a moment or two — or being rescued by their friends — then you’re doing something wrong. I’m guessing you came across as angry and potentially violent because you are angry and potentially violent, and you’ve made a self-defeating decision to cultivate an intimidating vibe. That shit repels people, HOPE, and you’re never going to get anywhere with women — or employers, for that matter — if you give yourself over to anger, violence and menace. Bearing this in mind might take the edge off your anger: Fully 15 percent of 21-year-old men are virgins, HOPE, while only 5 percent of 25-year-old men are virgins. So you have a better than 66 percent chance of losing your virginity in the next few years if you can stop 1) wallowing in self-pity and 2) giving yourself over to anger.
My advice: Get your ass to a doctor and a therapist. Medication can help with the depression, and a good therapist can help you overcome your anger, self-pity and violent fantasies. Getting help, HOPE, is the best way to increase your odds of getting laid or getting a girlfriend — or both.
Q: I’m a 25-year-old bi girl in the Southwest, and I’ve been with the same hetero guy for almost three years. I miss being with women. We made an attempt at being monogamish, but feelings were hurt and we went back to monogamy. He still parties like he’s in college and is a bit dependent on me — socially — whereas I crave independence and, quite frankly, pussy. I’ve started to withdraw and resent him, not just for the lack of sexual freedom but also because he drinks too much and acts like a slob. I want to move out when our lease ends. I’m willing to work on our issues, but I fear that when I have this conversation, it will break his heart and he will break up with me as a defensive approach, rather than seeing the breathing room as a way to work on our relationship. How can I express my need for other sexual partners and more space without sounding like I’m calling off the relationship? Is it even worth attempting dating, post-living together? —Insert Quirky Acronym Here
A: Here’s what you should say to your boyfriend: “You’ve got some growing up to do, and I’ve got some eating pussy to do. I don’t want to end our relationship, but I’m moving out when our lease is up.” If your boyfriend breaks up with you, IQAH, it’s probably for the best — and it may not be forever. If he does dump you for purely defensive reasons, then he didn’t really want to dump you at all, right? So once the shock wears off and his anger subsides, your boyfriend may decide that having you in his life is more important than having you all to himself.
Q: I am a heterosexual male. I was dating this girl for six months. We weren’t living together, but there were two toothbrushes at my place. We weren’t living together, but there were tampons and birth control pills in my medicine cabinet. We weren’t living together, but there was yogurt in my fridge. You get the picture. Anyway, things were going well until she told me about a friend-of-a-friend who was building a website for a local “swingers club.” I didn’t get outraged, and this outraged her. A four-hour discussion followed, during which I held my “good for them” ground, and at the end of it, I no longer had yogurt, tampons and birth control pills at my place — and I no longer had a girlfriend. All I did was not get outraged, and it cost me a girlfriend. Does this seem a little extreme? Am I crazy? —Her Ex Looks Perplexed
A: No, HELP, you’re not crazy. You’re lucky.
Send that friend-of-a-friend a thank-you note. Because if he weren’t building a website for a swingers club, HELP, you might still have tampons, yogurt and scented soaps in your apartment — along with the crazy, controlling, insecure nutjob who came with ’em.
Q: During my last relationship, I finally got to explore the kinkier side of my libido. My partner and I went to pro doms and sex clubs, and I got to watch my buddy fuck her. While the relationship was ill-fated, sex was not the problem. One year and some heartache later, I’m ready to date. But I don’t want a vanilla sexual relationship again. My problem is, I don’t know how to integrate this into my dating life. People ask to set me up, and I keep turning them down ’cause I feel like I don’t want to get involved with someone unless I know that we’re sexually compatible. And yet, I feel some internal angst about using FetLife or similar sites for dating, as if somehow I’m making sex paramount. —Nervously Avoiding Intriguing Vanilla Entanglements
A: Sexual compatibility is hugely important, NAIVE, and prioritizing it doesn’t make you a bad person. But the choice you’ve laid out for yourself — dating only kinksters you meet on FetLife or nice girls your friends set you up with — is a false one. Date both. You’ll have to establish emotional compatibility with a woman you meet via FetLife, or sexual compatibility with a woman you meet via real life. FetLife or real life, there’s some work to do at the start of any new relationship.
And don’t assume that a woman you meet through friends is gonna be vanilla. She met you through friends, and you’re not vanilla, right? It’s a bad idea to give someone a laundry list of your kinks on the first date, NAIVE, as no one — kinky or vanilla — finds that kind of emotional cluelessness attractive. Just say this when the conversation turns to sex: “I’m pretty sexually adventurous.” There’s a good chance you’ll get a “me, too” in response.
On the Lovecast, Dan finally enlists advice from an actual ethicist at savagelovecast.com.