Earlier this year, my girlfriend of 4 years broke up with me. During that relationship I was always seen as the charismatic, well dressed, confident guy. After the breakup, I took a couple months to really focus on myself. I dropped some bad habits, picked up healthier ones, got in the best shape I’ve ever been in, and overall felt strong mentally and spiritually.

After that period, I thought I’d be ready to jump back into dating casually. I assumed I’d be able to talk to multiple women, have fun, and keep things light. But the reality has been very different. It’s now November and I haven’t actually slept with anyone since my breakup and at points it’s killed my self esteem how hard it’s been for me.

I go out with a group of friends nearly every weekend to bars and clubs and I figured by this point just by chance I would get lucky and take a girl home with me, but no. I’ve been on some dates, but I’ve made mistakes like being too upfront about wanting something casual way too early. I also had a lot more approach anxiety than I expected. Now I’m stuck in this pattern where I feel like I’m chasing women. I get numbers or Instagrams, we talk but I always feel I’m putting in more effort, and I try to set up dates, but really my intention is to push it toward sex rather than seeing where things go naturally. And honestly, that mindset feels forced and stressful and not aligned with how I am confident in acting.

I also don’t want to keep spending money on date after date when I’m not looking for a relationship. I’m trying to figure out how people are getting friends-with-benefits situations without spending a lot of money for it. Are guys really out here just saying, “Come over” and it works? Because I haven’t tried being that direct and honestly it feels intimidating. I think I’m more of the nurturing, slow connection type, but I don’t want a relationship right now.

So I guess my questions are:

  • How do you move out of the “chasing” mindset and get into a dynamic where women also pursue you?
  • How do you express interest in something casual without sounding disrespectful or manipulative?
  • Is being direct (“I’m interested in keeping things casual and seeing where things go physically”) actually the move?
  • And lastly… how are guys getting into FWB situations without spending money on elaborate dates?

For context: I go out to the bars/clubs nearly every weekend just to pickup girls (but also try and have a good time with my lads). I’m fit, above average looking, have a good career trajectory, but I get nervous around attractive women and I don’t want to feel like I’m running “pickup lines” or playing games. (I feel I have low “game/rizz”)