So after many months of being in a relationship, I ended up having an extremely honest conversation with my current partner/girlfriend about how fucking hard it is being an average-slightly average looking guy in online dating.

Much to my amazement, my partner agreed with me on a number of issues. Here's some insights that she openly admitted to, and I felt would be useful for the community.

  1. Getting sex is easy for most women, but she was surprised how hard it can be for men. Yes, I know this is fairly obvious, but she straight up told me she was shocked when I told her I went without any sexual contact for four years, excluding a few kisses after semi-successful dates. She told me she'd have gone nuts after four months, let alone four years. She also told me that she found it incredibly surprising because she considers me to be above average in terms of looks (I consider myself average at best, although my style has improved drastically over the years).
  2. A lot of nice girls look for the bad boys for one night stands/casual relationships. Low level drug addicts. Guys who are assholes. Guys who aren't interested in them as people at all, but are just looking for a warm body to keep them company for the night. These are the guys many girls will take home with them or swipe right on when they're looking for something casual. This may seem nuts to decent guys, but it has a fairly simple logic to it: if a guy's an asshole, it's easier not to feel hurt if a girl hooks up with a guy and he never calls back. If he's a good guy and doesn't call her back, even if the agreement was for something casual, this stings a lot more.
  3. Some girls make little/no sense when it comes to sex/dating/relationships. She talked to me from her own experience, as well as watching what some of her friends did, that when it comes to attraction/sex/dating, she has no idea what made her and some of her friends make certain choices, particularly when they were younger. Her own words: "Girls are weird."Case in point: when she and I went on our first two dates she found it incredibly surprising that someone "out of her league" (in my opinion, I'm not) would have any interest in her. She was still dating to see what her options were, and between our first and second date a guy she went on a date with (trance party drug user who switched to weed because he was too broke to get anything else) kissed her. Despite feeling a strong emotional and physical attraction to me, after the second date she dropped me in "favor" of the other guy simply because he'd made a move first.When she told me she wanted to see where things went with this guy and turned me down for a third date (I didn't know the context then), I did what I call "putting my cards on the table". I told her that I was really disappointed that things had turned out this way, but I thought she was really cute and cool. I would respect her boundaries if we ever hung out at any point, but I made it clear that things were not platonic/let's just be friends from my side. What's interesting about this is she said she found this incredibly arousing. I knew what I wanted, and even though she tried to "friend zone" me, I made it clear who I was and what I wanted. This was when she realized she made a mistake, but it was too late for her to go back now.Not long after, the guy who had kissed her first broke up with her. Despite everything she still was pretty upset, and took the time to put herself back together. It was after this that she slowly started trying to find excuses to hang out with me, and after things didn't work out in terms of timing initially, one night she put her cards on the table and asked me what I was doing. Needless to say the rest is history.
  4. Even girls that are attractive and who you think have their lives together on the outside, can have really shitty self-esteem and not date decent guys as a result. Basically my gf got cheated on in her first relationship. Since then she considered herself "not worthy" of a decent guy and really only went for guys/relationships that wouldn't go anywhere in the long run because when it didn't work out, it didn't hurt as much, because she could see it coming.
  5. Keep it cool. Before my girlfriend straight out asked me to hang out with her one night, our paths crossed at a local event (turns out that was intentional from her side). She was surprised how relaxed I was despite how things had turned out, and it just made her want me more. Since then I've opened up a lot more with my past/emotions/history, but I wouldn't advise doing this too early.
  6. Get the deal breakers out of the way early. Don't want kids? Find a casual way to bring this up early on in dating. Looking for a partner but not necessarily marriage? Same story. You want to find stories/light conversations that bring up discussions that allow you to filter out women early. This was something I used to do, and did with my gf/partner on our early dates, and even though things didn't work out initially, she was glad I brought these things up because they highlighted important stuff she eventually shared that she would want in a relationship.
  7. Edit. Some girls really like to be chased. My gf and I didn't discuss whether she had done it, but she shared that some of her friends really liked some guys but never wanted to look too eager/slutty, so played hard to get.

Quick lessons to take away:

  1. Stop trying to figure out women. Know yourself. Know what you want. And go for it.
  2. If you're interested but aren't sure if you can go for a kiss, at the end of a date put your cards on the table and walk away. Tell the girl why you like her, that you're interested, and that she should call you if/when she feels the same. Then walk away. Literally. Tell her she doesn't have to give you an answer then and there. Some girls can be like a "deer in the headlights" after this sort of thing, so it gives them time to figure out what they want. If she reaches out, then you know you can proceed to physical stuff. If she doesn't, you just saved yourself a whole lot of time/energy.
  3. Vulnerability is for after you've hooked up. At the start of the relationship, you want to keep it fairly chill. Focus on fun, share the positive stuff, get physical, and don't let your emotions run away with you. If she's still around after a couple of months, or she starts to open up about things, then you can start opening up about the more serious shit.
  4. Edit. Just be honest. I'm now in my late 30s, and my life is a lot simpler since I adopted the "I'm getting too old for this shit" mantra to all aspects of my life, including dating.

I probably won't be back for a while. I just had this on my mind and wanted to share it.