Savage Love: Jan. 4, 2024

Virgin territory, stinky boyfriends and horny bosses

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Photo credit: Rachel Robinson

I’m a 28-year-old woman and I’ve never had a boyfriend or sex. I didn’t focus on dating in order to prioritize my education, career and mental health. I am doing very well in my life overall. I have two bachelor’s degrees and a master’s degree, a job that I love, I live in a great city (Chicago), and I’m doing well enough financially to buy a condo this year. The only thing I’m lacking is relationship and sexual experience. 

I am putting myself out there and going to social events to meet guys, but I’m holding off on having sex until I’m actually in a relationship and I’ve formed an emotional connection with someone. Casual sex has never interested me. I’m in therapy and I’m working with my therapist on my confidence as I navigate the dating world. My anxiety is my biggest roadblock. 

Nobody in my life has reacted negatively to my lack of experience, but my anxiety tells me that no one will accept me and that there is something wrong with me. My anxiety tells me that I am the butt of everyone’s jokes and that I’m a loser. 

I know that doesn’t make sense. Literally no one has ever criticized me for my lack of experience. My friends don’t care and have been supporting me as I navigate the dating scene for the first time. 

I guess if I had to boil this down to one question, it would be this: How do I stop being insecure and embarrassed about my lack of dating and sexual experience and be confident? 

— Nervously Experiencing Wonder 

Own the choices you’ve made about sex with the same confidence you own the choices you’ve made about your education and career. You were no doubt nervous AF when you got to college… and you nailed that shit. (Three degrees!) You were no doubt nervous AF when you got your first big job… and you nailed that shit. (Buying a condo!) 

Give yourself permission to be nervous AF during your first sexual experience, NEW, and trust your track record. You may have flunked a test or two, but you got those fucking degrees. You may have washed out during at least one job interview, but you got a fucking job. Your first time may be awkward, NEW, and you’ll definitely be nervous AF, but you’re gonna nail fucking like you’ve nailed everything else. 

I know it sounds like a paradox, but a person can be secure in her own insecurities. You’ll feel more confident if you don’t feel like you have to pretend to be any more confident than you actually are. And since you have a good idea who you want and what you want and how you want it, NEW, you’re starting from a better place than a lot of people whose first experiences came earlier in life. 

Instead of worrying that your potential partners can tell, NEW, tell on yourself: “I’ve never been with anyone sexually — I poured all my energy end effort into my education and my career — so we’re going to have to take it slow.” Some guys head for the door (of your condo) when they hear that, NEW, and not one of those guys will be the right guy. 

Remember: When you tell someone you’re inexperienced, you’re telling him one thing about you. His reaction will tell you everything you need to know about him. 


Have you ever seen a successful relationship when the sex was difficult from the start? Or even stopped pretty early in the relationship? 

I have been with my boyfriend since August, and I honestly lost my desire for him early on. He’s a bit of a hoarder and has some self-care and cleanliness issues, which I only realized some way into the relationship. It has killed the sexual vibe for me very early, but I do feel very safe with him, very connected emotionally. Is there hope? Or should we call it friends? 

— Only Doomed Or Real Shot? 

 I’ve definitely seen relationships succeed despite sex being difficult at the start. 

In some cases, the couple broke up, found new partners, and remained in each other’s lives as friends. But the couples that succeeded in the way you most likely meant — the sex was difficult at the start but they’re still happily together years later — had at some point redefined their relationships as companionate. Some of these companionate relationships were ethically non-monogamous (e.g., one or both partners were allowed to seek sex outside the relationship) but some were strictly monogamous. 

What I haven’t seen much are two people who didn’t share a strong sexual connection at the start manage to create one. And when I have seen that happen, ODORS, there was always some shared interest or dynamic or kink — there was always at least one thing that worked or clicked — and the couple focusing on their overlapping interests/dynamics/kinks and on that rock built a good-to-great sex life together. 

But what I found myself wondering as I read your question, ODORS, was why you would wanna make things work with this guy. If he can’t be bothered to bathe and brush his teeth and use a little deodorant when he’s trying to win you, ODORS, he’s not going to make the effort once he’s won you. There may be some underlying mental health issue here that he’s struggling with. You can offer him your friendship and moral support (provided you can spare the emotional bandwidth) but don’t offer him a blowjob. Sucking this guy’s dick would not only be unpleasant for you, ODORS, but it would send the wrong message to him, e.g., that he’s in good enough working order (Proof: He’s getting his dick sucked) and doesn’t need to get help and make changes. 

P.S. The sexless monogamous relationship as a concept has always broken my brain. If being in a monogamous relationship means you don’t have sex with other people, wouldn’t being in a sexless monogamous relationship mean only don’t have sex with other people? It has always seemed to me that if monogamy means, “I’m not fucking anybody but you,” sexless monogamy means, “I’m fucking everybody but you.” Perhaps someone who doesn’t wanna have sex with their partner but insists on sexual exclusivity — someone who thinks celibacy is a reasonable price of admission — can explain how this works or is supposed to work. 


My husband is the Membership Chair of a nonprofit in town. The organization has about 100 members. Some are cute/hunky/sexy. 

We’ve got an open relationship, but I feel that, given his position, he shouldn’t be having sex with these members because it might lead to jealousy issues among the others. He disagrees and brushes off my concerns. I’ve considered playing with a couple of them as well, but I have not because I am “the husband of” one of the club’s main organizers.

Am I wrong in expressing reservations about his playing with some members? And what about me doing the same? 

— Messy Ethical Matters Block Enticing Recreational Sex 

What kind of nonprofit org are we talking about? If it’s a group that works with at-risk youth (painting murals on underpasses or whatever) or some sort of social justice org (shutting down roads to airports right before Christmas or whatever), MEMBERS, the Membership Chair fucking his way through the members rolls could prove problematic. That goes double if being a member in good standing is a route to future professional success. If remaining in the good graces of org leadership means getting the kind of letters of reference or recommendation that help people land jobs or promotions, the leaders of the org — and their spouses — need to be conscious of their power and refrain from fucking members to avoid abusing that power. 

But if we’re talking about some sort of gay social club organized around a shared non-sexual interest (snowboarding, softball, kickball, etc.) or sexual interest (leather, pup play, kicking balls, etc.) — if we’re talking about a club that exists to help gay men break the ice and find like-minded friends and/or sex partners and/or romantic partners — then I don’t think the leaders or their spouses have to swear off fucking the members. 

Indeed, if the org was created to bring guys together socially and/or sexually, demanding vows of celibacy from the leadership not only punishes the men who step up to do the work (recruiting members, finding venues, scheduling events, setting everything up, breaking everything down, etc.), it makes taking on those responsibilities on less appealing. And if no one steps up to do the work, the organization falls apart — and who does that help? 

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