When and how do I “come out” as being sexually inexperienced in my 30s?

Q

I’m 36, genderqueer, and queer. I’m trying to date but I live in a place with a fairly small dating pool and I also don’t know how to date, which leads me to my need for advice. In my early 20s, I was in an odd, kinky relationship with a man twice my age while being mentored by his wife. He was my first kiss. Since then, I’ve kissed maybe 4 other people, all of them while I was out with my gay bff in Boystown, and that was over a decade ago. My health and being a caregiver to my family kept me from dating in my 20s “when you’re supposed to.” Now I’m feeling better, no one to have to be a caregiver for, and I’m finally living my trans queer life. But… I have a tiny piece of shame about being inexperienced (it’s also paired with a piece of shame from residual purity culture that comes out when I least expect it). I’ve been on first and second dates, and sometimes I think the chemistry is there but I’m so terrified about what they’ll think when I kiss them with what I’m assuming is the finesse of a 13 year old boy.

I’ve read books on how to be intimate with partners, how to ask for consent in an alluring way, etc — I’m book smart on sex. But practically speaking, I’ve only hooked up with a man every other weekend for a year or so, and that was well over a decade ago. Despite never actually dating anyone, I think I really want and crave a monogamous romantic relationship, but I would be willing to “hook up” with folks to learn what I like, how to pleasure my partner(s), and the whole aspect of being physically close with another human. I think this would probably be easiest to do with someone who was just looking to hook up and/or who is also poly. As long as there’s communication about what the relationship is and is not, I think it would be great.

When and how do I “come out” as being incredibly inexperienced sexually? I’ve heard kissing is like “riding a bike” but what if HE was a bad kisser, teaching me to be a bad kisser as well? What do you think is the best way for me to go about getting experience? How do I broach the topic of never actually dating anyone before to someone I want to date? I don’t want my inexperience to be fetishized by a potential partner. I just want to be in an equal partnership with someone, communicating, and having sex. Hell, I would love to just make out with someone. But I don’t go out to bars so most people I “meet” are through apps.

I really wish I could just write a personal for myself: “Fat genderqueer queer looking for laughter, fun, and fucking. Little practical sexual experience but I’m a quick study. If you’re looking for a good story, are kind, and are the type of person who’ll try anything once, why don’t you start with me?” and then field the emails and go by vibes and do a lil low effort hang to see if there’s chemistry. That would make it so easy. But nothing is that easy, I don’t think. Help!

A

Summer: So, I see two factors at play here. The first is that people can easily overestimate how much sex others are having. The second is that you’re talking yourself down a lot, which can get into your head and keep you from the sex you deserve.

On the first point, it’s perfectly ordinary to think that you’re sexually inexperienced and are behind others. Sexual experience and our ability to pull partners factors into our collective, societal self-esteem. The pressure is there and very real. It’s very easy to confirmation bias our way into only hearing extravagant stories about people’s wild sex lives and miss out on the people who are quietly living without a dozen partners a year. There’s definitely a survivorship bias thing, too. I’m guessing you wander through sexually open circles where people are likely to broadcast their escapades. But there are lots of people who go through life with less sex or don’t want to discuss it. Just because they’re not talking doesn’t mean they don’t exist.

Also, yes, sex is something that goes well with practice. But the practice should be fun. And it’s also fine to fall out of practice if you haven’t done it for a long time. The winning move is to find opportunities to practice again and embrace them. That’s a path to growth. From what I can tell, your ‘theoretical’ knowledge of sex and how to handle sexual situations sounds pretty well-covered. You do also have sexual experience to back it up. Rather than reading yourself as sexually experienced, which sounds like a much scarier state… I’ll ask you to try and picture yourself as a little out of practice and happy to make up for it with enthusiasm and learning. My advice? See yourself through that softer mindset, find some lovely, healthy kinky engagements and be upfront about your situation. I hope that fits your needs.

Em: Unfortunately, you just gotta go out and make mistakes. Sometimes it helps me to frame experimental time as “doing it for the plot” or “romanticizing my life.” If you go into a new encounter with the playful attitude that this is really just to add to your personal lore, it becomes more of a fun adventure. I know some people care about how experienced someone is, but if that’s something the person is really that concerned about, then don’t continue seeing them! They aren’t worth your time! You want to invite welcoming, healthy experimental energy into your life. If you’re already mid-fun and feeling this way, you can always leave and always say no. No matter what, you’ve learned what YOU do and don’t like, not what others think should be done. Each experience will have it own rhythm. Everyone involved in a first sexual encounter is figuring it out for the first time because they haven’t done what their doing with those specific people. Everyone starts out on a blank slate with new people, that’s the beauty of intimacy.

Additionally, have you looked into Lex? I don’t know what it’s like since I used it nearly four years ago, so I can’t vouch for it completely, but it’s a classified app for queer sex/relationships/everything under the sun. You could literally write what you wrote to us. 

Nico: I liked what you wrote! I also feel like people hop onto dating apps from all over the spectrum of sexual and relationship experience, and it’s totally fine to just be yourself about it. Instead of assuming everyone is lightyears ahead of you in terms of experience, maybe consider that there are likely other people considering putting themselves out there in almost the same way. Maybe you could find someone or someone(s) to hook up with who also wants to learn and explore and you can co-create a fun and safe atmosphere for yourselves. As for finding a long term relationship, I do think you’ll have more clarity on what you’re looking for and how to go about seeking it after you date casually for a little while. As for apps, Em suggested Lex and there’s also FEELD and even Bumble allows you to flag that you’re looking for casual dates / intimacy. The last two do require photos and aren’t really personal ads, but also, might I suggest trying to find queer speed dating events in your city? Even if nothing comes of it, at the very least you will have had to jump into the deep end when it comes to having conversations with strangers so you’ll know you can do it, and it might be a nice opportunity to practice some of your flirting skills.

Laneia: No real advice here but chiming in to say that your hypothetical personal ad absolutely SINGS.

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I’m in my 20s. This is the fourth funeral in five years that I’m responsible for organizing.

Q

Dear Straddle team,

You have so far helped me immensely with several of my very gay problems (yes, i definitely did need to stop stalking my ex’s insta stories, yes, that did very much improve my life, thank you). Now I come to you with a problem that has absolutely nothing to do with being gay, but that none of my friends can help me with because they just Have Not Been There, and I don’t know who else to turn to for this.

In 2019, my mom died. One year later in the same month my dad got diagnosed with cancer and a year after that, in 2021, he died too. In 2023 my grandmother (who practically raised me since my mom was always sick) died. Then, today, in 2024, I went to my aunt’s house because she hadn’t responded to my texts in a while and I was worried she’d killed herself, and I turned out to be right (I thankfully didn’t see the body because a friendly guy offered to go in ahead of me and before she died she helpfully put a note on the living room door to not come in and call emergency services instead).

I’m in my 20s, and none of my friends have ever lost anyone close to them, let alone a parent, let alone both parents, let alone lost someone to suicide. I am starting to think that I am some sort of death freak and I’m worried that people will not believe me when I tell them about my family, because the scope of this is just not something I’ve seen outside of like… war situations or much older people! And the old people I have talked to are just wholly unsympathetic to the fact this is all happening to me before I’m even thirty, for them this is par for the course.

This is the fourth funeral I am responsible for organizing, and I have to somehow figure out what to do with her things and the cat etc.etc.etc…. Even people in my life who have lost, like, a grandparent or multiple, have had their parents take care of all of this stuff. My sibling and I keep having to do this ourselves (and now they can’t even come here because of their visa situation). I wish I didn’t need to keep using this skillset but it just keeps happening. I have my sibling and one living grandparent, and one more aunt I am not close to at all, and that’s it, that’s my whole family. I just ended my relationship of over half a decade which is a whole ‘nother thing to grieve, I am freshly in grad school, what the fuck am I doing with my life??

I guess what I’m asking is: how do I meet other people who have gone through some sort of tragedy and stop feeling so insane and lonely in this situation? It feels like nobody understands me, except for my sibling who is going through all of this too. Do you know of any resources for this sort of thing? (Not limited to the US if possible, because I am Not There). Googling isn’t getting me very far. Maybe some book recs or something? I guess I need to tell my therapist back home too… By the way, I love everything Autostraddle has ever published about death, I have eaten it all up, so thank you so much for everything you have done for me throughout the years already.

A

Summer: People who suffer trauma are often forced to ‘grow up’ or shoulder responsibilities far ahead of time. Most of the time, we think of children in abusive environments who are required to develop maturity and survival skills at the expense of their childhoods. It’s all too easy to forget that our whole lives are spent growing and developing.

You’ve suffered a great deal of loss and grief during young adulthood. The kind that should have come much later had things gone to plan. That’s a deeply unfair experience and you’ve been forced to take on extra responsibility in the aftermath. It’s likewise unfair and frustrating that your friends don’t have a script for reacting to this because they probably haven’t been through this at all.

As far as possible, I think you should lean on your sibling. They’re in this with you and probably share some of the emotional needs and pain with you. There’s no better person to look out for you and vice versa, as long as you keep each other afloat rather than drown together. For online communities, I often look to Reddit. Despite its many shortcomings, it tends to have a supportive nook for everyone, such as https://www.reddit.com/r/GriefSupport/

Good luck, OP.

Em: I cannot imagine how deeply you’ve experienced grief, loss, and sadness. My heart hurts for you and your sibling. No one should have to plan that many funerals that close to each other all before they turn 30. Like Summer mentioned, you’ve had to quickly become an adulty-adult far before you’re due to be making end-of-life decisions. You’re ability to cope with these losses only shows how resilient you are. You gone through SO much, which is proof that you can get through these moments, too. I just wish you didn’t have to.

Since I’m not sure where exactly you’re located, I can’t offer super specific resources, but I would definitely encourage you to find a grief support therapy group. An individual therapist will be a great start, but adding in that group therapy piece will help you meet other folks who have gone through similar things. Looking into groups like these could be a good starting point. My next best suggestion would be to look into what types of support groups your school offers. If you’re attending school online, or if your school doesn’t have anything, I would suggest reaching out to a university closest to you just to simply get names or resources of grief support groups. Community will be your best antidote to isolation, so I encourage you to lean on your sibling and reach out to new friends.

Laneia: While our situations aren’t an exact match, I’ve also lost both parents far sooner than I expected to, and can relate to your feeling of intense community isolation during a time when you need that support the most. I’m so fucking sorry, and I’m so fucking glad you’re here. (Like, on this planet, in this inbox, on this website, in these comments.)

Earlier this year, at my absolute lowest, I miraculously stumbled upon a local grief center that deals specifically with traumatic loss. At first I wasn’t sure that my mother’s death rose to the level of ‘traumatic’, but I was reassured time and time again that yes, it did, and not only was the loss itself a trauma, but the time surrounding my mother’s death and the events that unfolded in the months that followed were also traumatic, and that all this trauma was playing a continued role in my inability to keep my head above water. That reassurance was a lifeline. If you also need to hear this, please allow me: you have experienced compounded traumatic loss. Both you and your sibling need (and deserve!!) a dynamic, trauma-informed support system. 

My grief center does 1:1 talk therapy, group therapy, and provides spaces and resources for somatic relief (both privately and in a group setting). I also learned there are a surprising number of local places (I’m in AZ, but I’m guessing/hoping this isn’t unique to this state/country) that focus on grief and healing through animal care — like working with horses, for example — nearly all with sliding scale options. I haven’t personally attended anything in this vein, but it seems to be deeply healing for those who have.

Here are a few online/reading recs that have helped me:

Rachel Cargle — Of everything I’m listing here, Rachel Cargle has been the most pivotal. She’s truly a gift on Instagram, and you can join The Great Unlearn where she hosts Waves sessions that offer a creative community space for processing grief. She’s also done and continues to do incredible work outside of grief. 

Alua Arthur — Alua is a death doula and author, and I get so much from her Instagram as well: Going With Grace.

Modern Loss — If you’ve found solace in Autostraddle, you might get their Modern Loss Handbook — it’s just as frank and honest and messy as we are, and I’ve loved it.

Good Mourning — This began as a podcast (the hosts met at a grief support group after both losing their moms, one to suicide, which she doesn’t shy away from processing) and has recently grown to include a dedicated online community.

The Year of Magical Thinking — No AS list is complete without a little Didion, even if it’s repetitive. I’ve reread this book at least four times in the last two years, and I get to touch a new texture of grief each time. I mean, it destroys me, but that’s also the point.

Conscious Grieving: A Transformative Approach to Healing from Loss — Claire Bidwell Smith has built a whole world of grief counseling and support, including retreats and 1:1 sessions. I found her book to be very helpful, but you might want to go immediately to her Resources page and Grief Professional Directory.

Lost & Found: Reflections on Grief, Gratitude, and Happiness — When you’re wanting a more meditative, philosophical tour through this specific human experience, and you’d love a queer guide, please let Kathryn Shulz lead the way. This book is gorgeous and Exactly My Shit. I felt lighter for the first time in a long time.

Hello Grief: I’ll Be Right With You — This one’s a wee little book of drawings and poems and words by Alessandra Olanow that walk with you from the initial shock to the part where you can eat more than a bowl of rice with soy sauce and yesterday you laughed out loud for a minute and yeah you’re for sure going to live through this (which yes, is its own horrible reality).

Bearing the Unbearable (I simply cannot keep adding these subtitles, but rest assured there is one) — This book may or may not hit for you. Joanne Cacciatore is a grieving mother, and I found some unexpected comfort in the moments of rightful anger she recounts here. She also runs Selah Carefarm, a retreat for traumatic loss in Sedona, AZ. Like what if you went? What if you dropped right into yourself and the universe at Cathedral Rock? What if.

Grief Is Love — Full disclosure I have not read this book by Marisa Renee Lee in its entirety, but I sure did read the Kindle sample and it’s on my TBR list.

The Crying Book — Did you ever read The Sound of a Wild Snail Eating? This is kind of like if that book ran into Lost & Found on a wet fall day and decided to grab lunch with the Ologies podcast, you know?

Finally (sorry, hope you wanted a mini treatise), and I’m positive you already know this, but please do take care of you. Eating nourishing foods and putting yourself in the way of sunlight and advocating for your own peace when you can, will not actually solve a goddamn thing — you know this! — but it will help you get/stay slightly above the worst of it when the worst of it descends. I hate that I can’t promise I’ll text you later to check in, but please know that I’ll want to. My love to you, your sibling, your grandparent and aunt, your mother and father and grandmother and aunt, and to your whole life. I am so fucking glad you’re here.

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