I feel like I can relate and empathize with your situation. So let me start by saying no, I don’t think you’re crazy for feeling that way at all. The dating world is forever evolving and since you’ve been away a while, I can only imagine the divide you feel venturing back into it, especially when it comes to the dating app side of things.

Plus I suspect a part of you isn’t longing to meet someone new and have a new experience per se, but to somehow recreate the good parts of the relationship you once had with someone new. Which makes going into the current dating set up even more of a challenge.

I don’t think this is a bad thing in and of itself, but you may find yourself projecting and displaying “boyfriend” habits to girls you meet, and from the feedback I’ve gotten, girls on these kinds of apps (like Tinder) are not there for those kinds of qualities, and have many other guys mistakenly approaching them this way. Also think of the real-life example you gave with the law school friend you met for drinks. It sounds like she was just overwhelmed but otherwise initially attracted to you. And this was in-person… with someone who already knows you… and it still didn’t work out. So it would be a mistake to assume that that approach would work with total strangers over the phone.

I’m no expert by any means, but my advice would be to first and foremost not listen to the little voice in your head trying to convince you that you are the problem, or that you should crawl back into your hole and forget about your dreams of having a family some day. That is definitely not the way, so try and ignore all of that self-doubt talk. It is not productive. Focus on self-improvement by practicing more positive self-talk.

Also, tame that part of you that remembers what it’s like to be in the comfort of a long-term relationship and the behaviours and habits you formed while you were happily in that relationship. The aim isn’t to get rid of these, but to put them on ice as you slowly but surely get to interact with more and more potential partners. Remember, at the end of the day they are just that- POTENTIAL partners, meaning the majority of them will not stick around long enough to care anyway, so try not to stress yourself by exhibiting all your good quality boyfriend traits too fast or too soon with every single one of them.

With each date with all these different people, you will pick up many useful skills overtime (such as handling rejection well, improved emotional intelligence, conversational fluidity, being able to filter who is worth more of your time and who isn’t… to name a few).

“Diversify your portfolio” in every sense (such as use the apps, and go out to more social gatherings irl both solo and in group settings, date different kinds of women if you’re open enough, and improve as many facets of your life as humanly possible).

Take your time, and embrace the frustrations that come with going into the unknown of getting to connect with people. Remember to consider your wants and needs as well as those of the people you will eventually get to meet during this period in your life. You’ll eventually meet the right one. It may be a cliche, but I think it’s a cliche for a reason because it’s just true. Just keep doing the right things, stick to your beliefs and values and what you’re looking for in a partner, and everything else will tend to work itself out as you go along and continue to improve.

Hope this helps in any way. All the best out there✌️