Hi, I’m 29m.

I broke up with my 1st gf in 2017, around 6-7 years ago. We met on a uni night out, and despite being very intimate, we didn’t have sex for a while. Since then, I’ve had various casual experiences, including one-night stands, friends with benefits, and casual hook-ups, and a few dates but not many (and not many 2nd & 3rd dates).

Speaking to women and getting attention at bars has never been difficult. As I’ve aged, both my casual interactions and the frequency of dates have decreased, partly due to reduced bar visits and changing dynamics on dating apps (either fewer people use them or fewer people my age/searching my age use them).

In the last 6-7 years since 2017 (ie being single), I’ve been on 1 or more dates with only 2-3 women I genuinely liked, but they weren’t interested in me. There were also instances where the roles were reversed (I wasn’t interested & they were). Female friends attribute it to me being unlucky, but the prolonged period makes me think it’s too long to just be unlucky.

Modestly, I acknowledge positive aspects of my life, including financial stability, physical fitness, an outgoing personality, hobbies and interests. Despite this, my struggles persist in getting past the first or second date. The initial comfort of meeting my ex in a casual setting contrasts with the forced atmosphere of formal dates. I appreciate this isn’t the way dates work but usually once I’ve had sex with someone, both me and them feel more at ease with one another and comfortable in each other’s company.

I seek insights into why I’m facing challenges in dating, especially progressing beyond initial encounters. Feel free to ask for additional details if needed.

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