36M — Never Had a Girlfriend, Feeling Behind, and Not Sure What to Do Next

Hey everyone,

I’m a 36-year-old guy who feels really behind when it comes to relationships. I’ve never had a girlfriend, never been in a relationship, and honestly I’m not even sure how uncommon that is anymore. Dating — it just never lined up due to shyness, lack of going out as a kid and not so great childhood trauma of abuse, and maybe choosing the wrong environments to meet people.

For context, I’m a nerdy cosplayer and pretty involved in conventions and horror/gaming communities. I stay active, take care of myself, and have a large circle of friends throughout cons and out, but for some reason dating has always been the missing piece. I’ve tried dating apps for years (paid versions too), paid matchmaking, putting myself out there at events, even building my own dating site to try something different, which made Boston news— but nothing has clicked so far. I have not much dating experience and had my first date at 30, and not so much luck since then mostly all off apps.

I’m at a point where I don’t know if I’m doing something wrong, if my inexperience is scaring people off, or if I’m just looking in the wrong places. I’ve put in alot of energy and efforts into this and felt in the end it doesn’t even matter. I’d really appreciate honest advice from people who started dating later in life or have been in a similar spot.

How do you actually break out of this cycle when you’re starting from zero in your mid-30s?

•	How do you bring up inexperience without oversharing?
•	Where do people actually meet others these days if apps aren’t working?

•	And how do you stay hopeful when it feels like you’re decades behind everyone else?

Any guidance or perspective would mean a lot.

Thanks in advance.