#149: Should I try to be friends with someone famous?

+ is 36 “too late” & am I straight?

Good morning!

Welcome to the last Sunday of the month, which means it’s time for Dear Baby. Today I’ll be answering questions about:
1. what to do when confusing sexual experiences have you questioning your sexuality
2. whether it’s creepy to pursue friendship with someone famous or well-known
3. whether it’s ever realistically “too late” to completely change your life course, even though we all romantically pretend it never is.
Don’t forget comments are open at the end! I’m always happy for questioners to get extra advice in case I’m wrong. 🤠

On Tuesday @ 9am, look out for a brand new episode of Dear Danny, where we’ll be answering five more questions. As always you can leave a question in our voice mailbox at 802-404-BABY or write in with a question here.

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On confusing sexual experiences

“Dear Baby, I’m a historically straight, cis-woman in a super solid, loving, respectful, monogam-ish relationship with a straight cis-man, ‘Henry.’ At the beginning of our relationship a few years ago, I had been very transparent about my desire to explore my sexuality with women and in group-sex scenarios, and Henry was happy/willing to support that exploration either via solo hook-ups with other people or via threesomes. We both share a fantasy of finding a woman that we like hanging out with and having a casual, once-a-month hookup. However, I’ve had a handful of solo hookups (with men and women) and threesomes with Henry over the past few years and I’ve felt pretty mixed about them. This mixed reaction has left me feeling *extremely* confused about my sexuality and make it difficult for me to trust myself. 

For a bit more context: I have only been in relationships with men, but have been on dates with women and have had sex with a handful. During sex, I usually enjoy it! I’m turned on, I usually orgasm (as opposed to hookups with men, lol), and I have a fun time. But after, I feel pretty ambivalent about it happening again…and in the morning, I don’t think about it that much. I don’t feel giddy/excited when they text me, and I let the relationships fizzle. Also, one other piece of data: I love lesbian porn, but I think it’s because I don’t like the male-centricity of hetero porn. 

Most recently, Henry and I went on a drinks date with Erica. We all had a great time and decided to meet up again. We hosted Erica over for a second date at our apartment last night. We were all expecting to have sex…we had cleaned our sheets, I had put on cute underwear, we had eaten a dinner that wouldn’t make us feel too full, etc. After about an hour of drinking/chatting, it was getting late, and I knew someone had to make a move soon or it would be too late (we all had work the next day). I found myself overwhelmed with a feeling of not wanting to hook up. I announced this to the group, they were disappointed but understood, and after another 30 minutes of chatting, Erica left.

I’m not sure how to proceed. This isn’t the first time I’ve called off a threesome mid-date. I feel bad disappointing Henry and stringing along our dates. When I’m horny, I want to have sex with women, but when I’m not, I don’t want to AT ALL. Is this erratic attraction a product of my sexuality? Of my anxiety? If I think that I will get into it, is this just something I have to push through? (Like not wanting to exercise, but feeling good when it actually happens?) How would you recommend I continue to experiment with this without dragging my partners along?”

I totally get why these experiences have left you confused! They would confuse me too. My main advice is to seek out some trusted confidants in the queer community and ask for their advice (or if you’re feeling shy about that, therapy or online forums could be helpful too). People who have lived with similar confusion and come out the other side of it will have a much richer perspective than I do. For that reason I’m going to keep this high-level—I’m only responding because I have a couple things to say based on what I’ve learned from friends with comparable experiences. And maybe some Dear Baby readers who relate can offer some guidance in the comments, too.

A lack of interest in women post-sex and wavering interest in them pre-sex could mean so many things, so I think you’re right to second guess the tidy conclusion that because of these experiences you’re not “truly” interested in women. Shame and sex are deeply intertwined, and your relationship with your desires, however complicated or imposed by societal forces, will inevitably affect how you feel before, during, and after sex. Your relationship with your sexual partners will impact this, too. If you’ve ever experienced a lack of interest in Henry because he’s been annoying you around the house, or because you’re not feeling good about yourself, then you know it’s possible for non-sexual hangups to impact your desire. I think most of us understand this intuitively, but it’s easier to just assume desire exists in a vacuum (e.g. “I don’t want to have sex because I’m just not a horny person” or “I want to have sex all the time because I’m just a horny person”), and that leads to a lot of self-misunderstanding. It has for me too.

Regarding queerness specifically, multiple friends have told me that before they fully embraced or understood their sexuality or identity, they felt disgusted after sex, or contrastingly, completely unburdened of whatever desire initially drove them to have sex in the first place (I’ve even heard that for some people, orgasm can soften gender dysphoria, leading them to feel temporarily “less trans”). Either way, the pre-sex feeling was gone. I think it’s easy to see why people who experience this confusing shift might then conclude that their desire is simply a kink, or somehow irrelevant to the rest of their lives. But I think the exact opposite can be true. For my friends, that intense emotional shift was actually a product of their unresolved feelings and shame around their desire or identities, and resolving that uncertainty did away with the roller-coaster entirely.

I’m not saying this is exactly what’s happening to you, especially because key details are different! I only share it to remind you that confusion can be an invitation, if you want it to be. I think that’s true in so many aspects of life, when we wish our desires would present as clearer than they are. It may feel safer in those moments to think, well, if I don’t want it all the time, I must not really want it. But oftentimes that clarity we long for only comes after more experience, rather than before it. Initially, the inkling may be all we get. To be clear, I’m not suggesting you ignore gut feelings—I think it’s great that you feel comfortable calling sex off when it doesn’t feel right. That’s not the kind of discomfort to push through like you’re at the gym. But maybe this ambiguity you’re experiencing is just evidence that you don’t quite know yourself in this way yet, and need exposure to more experiences and perspectives to help you do that. I hope you find them!

On 36-year-old regret

“I’m 36 and, honestly, for the first time, I have let myself fall into regret. Regret about my career and the long road it’s been (I’m a doctor) only to realize I hate it and now I feel old. People say you’re young and you can switch things up, but can you really? Actually? With loans and financial burdens and time? If we’re being dead honest, how old is actually old in terms of still developing? We say we’re young but we also judge the people who don’t have their life figured out by 30 or 40. At least I’ve had friends who do. Sometimes I feel like we’ve moved backwards. Most times I have no idea what’s going on. Hah thanks for listening!”