29M, only had one relationship and struggling to actually connect with women. What am I doing wrong?
I'm 29 and a half and I've only ever had one proper relationship. It lasted about 4 months, but I was genuinely on the verge of falling in love with her. We got on really well and were very compatible, but she didn't want kids and I do, so unfortunately that was a dealbreaker.
I am not inexperienced with women. I have slept with 20+ women. I've had one night stands, FWB, slept with attractive women, older women etc. I was honestly a bit of a whore in my early 20s. But most of that was very transactional and I never really learned how to build a romantic connection with someone. I grew up with two brothers, dad and my mum, and didn't have my first relationship until 25, so I don't think I ever really learned how to be romantic/flirty. I learned how to sleep with women before I learned how to actually date them. That being said, all those sexual encounrters bar 1 were from dating apps. I have only picked up one women from a bar in my life.
Looks-wise I'm probably reasonably attractive. I'm 177cm, pretty built and well above average in terms of physique/aesthetics. I'm around 20% body fat at the moment though and probably need to lose 7-8kg before I'd feel completely confident in how I look.
I'm probably an introverted extrovert. On dates I tend to just talk to the woman normally, get to know her and see if we get along. If there's a vibe, I'll gradually become more flirty. That's how it happened with my ex and it felt very natural.
But I recently went to a matchmaking/speed dating event with one of my mates and it made me question whether I'm doing something wrong. He's extremely extroverted and naturally flirty. He'll just walk up to women and start chatting to them, and his first dates usually last hours. One girl mentioned that Kinder Bueno was her favourite chocolate, so during their date he randomly took her to 7-Eleven and bought her one. He's just really good at creating that romantic/sexual vibe. At the event, I had one date that was basically platonic. That being said, he does not do well on dating apps, and hardly uses them. Another I thought went pretty well — we were flirting a bit and there was some touching — but afterwards she didn't even accept my Instagram request.
I also went on a Hinge date with a Peruvian girl recently. The first half hour was pretty platonic and I wasn't massively attracted to her, but eventually we started getting more playful and she actually asked me out again. We went to an art gallery the next day. I was pretty nervous because I hadn't been on a date in over a year, and after about half an hour I started trying to get a bit closer and more physical. She kept pulling away and eventually ended the date after about an hour, saying she didn't feel anything. I'm starting to wonder if I need to actually learn how to flirt and create attraction rather than just hoping it happens naturally.
I've also moved from NZ (Auckland) to Australia (Melbourne) about 18 months ago, so I don't really have the same social circle I had back home. One of my mates started salsa dancing and met a couple of women through it, which makes me think maybe I need to get out and actually meet more people. Although I have absolutely no desire to dance salsa.
Do I need to change the way I date and become more flirty/proactive, or am I overthinking this and just need to meet more women and let things happen naturally? It is starting to get me down as I swear all of my mates are in relationships and have had a few lasting a year or more, not 4 months. I know comparison is the thief of joy, but damn as I get older it is really hard to not let affect me.
I don't want to become some fake pickup artist. I genuinely want a proper relationship. I just feel like I've had plenty of sexual experience but almost no romantic experience, and I'm not sure how much of a disadvantage that actually is.