The Weirdness of Becoming Attractive in Your 30s

The Weirdness of Becoming Attractive in Your 30s

Okay I'll take a short break from coding to talk about this this morning since apparently it's interesting and I will do my best (as usual) to make it as not cringe as possible... because the point of talking about this isn't "gee guys, look at me!"

But rather to talk about the very weird experience of going from feeling bad about your body and attractiveness for most of your life to suddenly not and how it's confusing and exciting and challenging.

So as you can probably imagine, I've had a very complicated relationship with my body and my physical appearance for the first 30ish years of my life.

Let's unpack that for a sec. I had "girlfriends" all through grade school and middle school but was also very much a nerd.

And in my working-class midwestern town, it was not popular to be the smart kid who was also a political outsider (liberal parents) and didn't have the best social skills (ADHD/limited self-awareness).

When I hit puberty I shot up fast and realized girls liked me sometimes.

But internally, I was having a ton of gender dysphoria and body confusion and *I* didn't like me much.

Still, I liked other people. But then I had my first sexual experiences pretty young (probably too young in retrospect). I was 13, my girlfriend was 12.

Looking back I feel kind of awful about this relationship because it's very clear to me as an adult that she had experienced some sexual abuse in her life and was processing this in her own way. We never actually had sex but there was a lot of oral and a lot of codependence.

And also it set a totally unrealistic expectation for me about how quickly relationships were supposed to become sexual--later girlfriends in high school were not as ready to jump into intense intimate situations and this was very confusing for me, and I internalized this.

Because when you go from a solid year and a half of thinking you're in love and having routine sexual experiences when you're 13 to basically not that for the next four years, it's a real mind fuck.

I blamed myself and felt totally unattractive instead of understanding that my first relationship was unusual both for it's intensity and the casualness of the intimacy for our age. This was also heightened by my dislike of my own body. Massive self-esteem issues.

So I had girlfriends and kissed a few boys but other than one drunk terrible night where a casual encounter started and then stopped because we didn't want to risk things without a condom, I didn't really have sexual experiences again until college.

In college I didn't even date--I latched onto a partner VERY quickly in the dorms within the first month of Freshman year and we had an extremely co-dependent relationship for seven years (that was my ex-wife).

I think I had extremely romantic and idealistic notions of love and what I wanted for my life and I was just so excited to be in love and have someone who I liked and who liked me and nothing to compare it to (because I didn't really date as an adult). But I still felt ugly.

Again, because I didn't really understand how relationships develop over time, I never stopped to consider whether we were actually compatible--I think I told her I loved her within 5-6 weeks (and I did, looking back, but it wasn't the selfless love that I imagined it was).

And I also didn't understand that 1) libidos could be mismatched and 2) that attraction is more than physical--I think I acted in ways that were unattractive as a partner a lot (I was pretty selfish, often). I don't know. It's hard to look back and really unpack the situation.

Because I never really got the other side of it from her and I can't ask her now so all I can do was guess.

But, for whatever reason, I felt like I was always the one initiating our romantic encounters. This was also very hard on my self-esteem because I felt unwanted.

And I struggled with this because I didn't want to make HER feel bad about it, but I took it very very hard and it magnified both my self-esteem issues and my dysphoria. Like "of course I'm unwanted, I'm ugly. I'm lucky she's with me at all."

Because I didn't date anyone but her, I had nothing to compare it to. So I just kind of hated my body on multiple levels and felt like a complete loser who was totally unattractive. Physical intimacy was very important to me. It was not as important to her. More self-blame.

And obviously I was internalizing a LOT of self-loathing as I ramped up into my transition in my early 20s, because if you think I felt unattractive as a man, gosh--I felt like a monster when I was trying to present as a woman.

Which is a little funny to me now because when I look back at pictures of myself pre-transition, I was not at all unattractive. And I had tons of tells to clue me into this, but I wasn't savvy enough to internalize them.

And transitioning was very hard. Things were still pretty different back in the mid-2000s, being trans was not mainstream, and I felt like people were totally justified reacting to me with revulsion when it happened.

I guess this was actually the late 2000s, early 10's but whatever. It was not like it is now.

I felt lucky that anyone would want to date me and that it was a fluke that had way more to do with being interesting than being attractive.

I would go out on dates and feel flattered and grateful when any of my relationships would progress (however quickly) toward sex because I still had DEEPLY internalized that I was unattractive and terrible. It was a very unhealthy way to see myself.

And when I met my future husband, who has always maintained that I was beautiful and attractive, physically and otherwise, at all points throughout our relationship, I couldn't internalize it. I never believed him. I always thought he was flattering me.

Because I was still too in my own head and seeing myself through my extremely judgmental and negative eyes. I fixated on things I hated about my body and all the ways I didn't measure up to other people and just had a terrible relationship to my body.

And this continued with little improvement for years. No matter how much reassurance and external signals I got that I actually might not be ugly and unlovable, I couldn't believe it because I KNEW how unattractive I was. Anyone who told me otherwise was pitying me.

And somehow along the way I started just accepting it and getting on with my life anyway because what else can you do, and stopped worrying about it so much.

This was actually the first step toward starting to love myself and I didn't know it at the time

Who'd have thought that not actively hating and judging yourself all the time might be good?

So I stopped hating what I saw when I looked in the mirror and just kind of accepted that people were lying when they said I was pretty but I didn't care.

And I started working out a lot more again and got better at my hair and makeup as these things became very normal.

But most importantly I worked on my social skills and being a more empathetic person I could like better and also self-awareness... I worked on this HARD.

And weirdly enough developing more empathy and more compassion and listening more and being more respectful of other people started working its way into my feelings toward myself... and I started hating who I was a little less.

And also getting over my self-loathing about who I was had a magnifying effect on my ability to relate to both myself and other people because over time that started turning into confidence and easiness that made me seem less like a lonely, intense, downer all the time.

I used to be very much like an angry-at-the-world depressed person and this was no longer the case (think JD from Heathers except less desire to hurt people and more self-blame).

I started developing more humor and lightness in my personality.

To the point where a lot of people in my life commented on the change. @eigenrobot mentioned this in our conversation on my podcast, many of my family members have noted it, and friends too who have known me throughout.

But it's still pretty hard to undo 20 years of self-loathing and hating your body, and I still struggled with self-love in spite of my progress. It actually wasn't until I had a drug experience with MDMA less than 2 years ago that I really had a big breakthrough.

I am not endorsing illegal drug use but this experience was absolutely life changing for me because for the first time (possibly ever) I understood what it felt like to love everyone around me (including myself).

And that understanding helped me to see how much my usual internal narrative about myself and my body was SO incredibly damaging. This changed everything for me because I saw that it was possible to have love and compassion for myself.

Anyway, that began a journey to build more of those feelings toward myself all the time... independent of any substance. I had a new goal. And I actually understood what I was shooting for because I had _experienced_ it once. I don't think I had ever actually liked myself.

And this progress continued to have a self-reinforcing positive feedback loop where I liked myself better, I didn't feel hurt and anger toward other people for rejecting me (whether or not they actually were), and I started liking my body a lot more. And this came through.

So I worked hard on actually feeling like maybe I was pretty, maybe I didn't have to hate myself, maybe I was attractive, and I started realizing the power inherent in being able to help other people feel this way too. Again, I got kinder and a little softer.

And (while this is still a work in progress) I got better at presenting myself with tact and subtlety, without self-conscious bravado that feels like desperation. I started just feeling a little more comfortable in my own skin.

And I think this has come through in a variety of ways when I interact with people--messages, communication patterns, pictures. I'm less self conscious and less afraid. A big part of why I'm so open here is pushing that work forward.

Developing vulnerability and putting yourself out there and seeing that your self-perceptions may not be entirely accurate or universal is a huge part of building self confidence. We're our own worst critics.

And also, remember that I spent most of my adult life in two very serious and committed monogamous relationships, and struggled with sex in both of them for different reasons. I had two data points until I started dating again, during periods where I actively hated my body.

Anyway, my experience on dating apps and at clubs as I developed more easiness and self-esteem and reduced my fear of rejection was... shocking for me.

(And this is where I don't want to sound braggy, I'm very sorry if you are struggling with this, I hope this thread helps.)

But it blew my mind when I would go to dance clubs or message with people on apps and pretty girls (and guys) not only tolerated me talking to them, but actually seemed to WANT me to talk to them and appreciate my interest in them and their lives.

Because I'd spent so much time assuming that people were doing me a favor when they showed me any affection or interest that it had never occurred to me that they might enjoy me offering them the same. Suddenly this clicked for me...

And I realized for the first time that attraction is as much about how you make other people feel as how you look (and arguably much more important). This completed a puzzle piece in my communication style that had always been missing.

And it was so weird because I suddenly had this massive wave of empathy for everyone around me and I wanted everyone to feel special and pretty and liked because I knew how much it hurt to not feel that way.

So again, I spent more time being actively interested in other people and trying to make them feel good and got more feedback loop results where I got positive attention in response and I felt amazing that I was able to make other people feel good and happy too.

And this has kind of snowballed... I'm just easier with people and more sympathetic and compassionate to them and myself.

This has had a massive impact on my dating life that I never could have imagined.

And now I find myself in this weird place where I like who I am more than I ever have before, and I'm happier than ever before, and it just keeps self-reinforcing (albeit not all the time, y'all see my emo posts too).

And suddenly dating just got... easy. I have women messaging me and happy to talk to me and telling me I'm gorgeous and accepting my compliments... and sometimes the people I date want me to send more intimate pics and I'm like "you can't possibly want that." 😳

And it's so fucking WEIRD.

Because then I send the pics and they appear to like them and I still can't quite believe it and am embarrassed to even talk about it.

It still kind of feels surreal.

I have three dates this week with really cool, accomplished, attractive women.

I have half a dozen message chains going.

I don't quite know what to do when these get kind of intimate and they often do, I'm still sort of stunned.

Because not only did I spend 20 years hating myself, I've also never really experienced dating when I didn't hate myself and feel awkward and self-conscious.

It's weird re-contextualizing who you are to yourself when you're in your mid-30s.

But ngl it's pretty awesome.

And I genuinely want everyone to be able to feel good about themselves in this way.

Because not a lot has really changed except I learned to love myself more and got better at making other people like themselves too.

So it's very much a feeling of excitement and disbelief and I still can't quite accept that these people find me attractive but apparently they do!

It doesn't feel real... feels like I'm re-defining my entire perception of who I am in the world through my own eyes.

And also it's strange and a little scary because I don't really know how to be an attractive person? I don't quite know how to explain this feeling. 🤷‍♀️

Something about my identity feeling shifted and feeling awkward and sort of disbelieving the attention, and super embarrassed about it because I feel like I'm not supposed to acknowledge it or talk about it because I'm afraid people will tell me actually I'm wrong about that or punish me for being a thot or whatever.

I don't know exactly. The feelings about it are complicated and hard to convey.

All this to say becoming more attractive as a 30-something adult after so many years of NOT feeling that way are simultaneously exhilarating and confusing and uncomfortable but also awesome. 🤷‍♀️

Very much ugly duckling vibes going on over here.

Anyway, that's my experience. It's very weird.