It was good! But something came up, and I’m hoping to hear GT opinions.

ETA: This whole situation described below is a nope...the date ultimately was good cause it got me back out there and there was no way of knowing beforehand that the dude was a dud (read below, warning: description of manipulative behaviour) Trying to rationalized horrible choices and actions, on my part and on his part (especially), is a no-no. Thanks commenters for making me realize that my gut instinct on this was good and that he tried to exploit my vulnerabilities. Original post follows. 

So first off, I signed back up for online dating to give it another go a week ago. I sent a message to this guy last (I’ll call him Mr T.) night and we ended up on a lunch date today. There was good chatting for three hours!

We were very open and honest about past relationships and baggage from the get go. He’s in the process of getting divorced and has 4 (!) kids. None of this is a dealbreaker for me. (there’s a “but” coming later on....) We told each other our life stories. On my end, I told him everything - my less than happy childhood, my depression issues, my suicide attempts, my financial issues and what happened with my ex. And he was totally fine with all of it. He though my ex reasons for breaking up were immature, and made the observation that me and my ex never discussed “heavy” things (he’s totally right). (Side note right after lunch, I went and had a coffee with an old friend who I hadn’t seen in years and he got the whole story of the ex as well, and my friends reaction to my ex dumping me was the same as Mr T - that, yes, I made a mistake but it was a dumb ass reason to dump someone. There was something very validating hearing from two separate men - one whom I just met the other who I’ve know for 15 years - have the same opinion. It made me feel less ashamed of what happened. And less afraid in general that I was going to be rejected for the rest of my life based on my issues. But I digress).

For Mr T. there’s a big BUT. BUT... he was open about the catalyst for his divorce and it’s not good. He had been unhappy in his relationship for a very very long time, but due to his own issues, stayed to try to make it work. Plus, ya know, 4 kids.

So the final catalyst for breaking up with his ex was: he’s a teacher and ... his 17 year old student fell in love with him and he fell in love back. He knew that his and her feelings were getting out of hand and that it was beyond inapropriate and that he couldn’t have her in his class anymore. So he told the administration of his school what was happening knowing full well that he would lose his job. Which is what happened, him and the administrators felt it best if he left and they wrote him a letter of recommendation. After he left his teaching job, Mr. T. and the student would see each other from time to time and kissed once - after which he stopped the relationship and told her that she needed to tell someone what had happened so that she wouldn’t have to keep it bottled up inside her and for the fact that it was obviously impossible for them to be together. She told her aunt and the aunt called the police. There was police investigation (of which he was totally cleared) but he can’t contact the student again.

When he asked me what I thought, I told him that I needed to sit with the information for a bit because that’s a lot to take in. He thought that my response was really reasonable and that he would understand if it was just too much for me to get past in terms of us dating.

So, on the one hand, my reaction is “Holy fuck dude, what are you doing falling in love with your 17 year old student!”...on the other hand, he was completely up front and honest about the whole thing from the get go. We can’t control who we fall in love with and nothing happened beyond that kiss. He was upfront to the administration because he needed to remove himself from the situation. But he still fell in love with a 17 year old.

So my gut is going in two different directions on this one (as per the previous paragraph). I think I need a bit of time to process and would like to get to know him better since we had a nice time out to lunch. On the other hand, this seems like the kind of things friends would say “RUN THE FUCK IN THE OTHER WAY TRACTOR GAL”, so that’s why I’m hoping for some GT perspective.

However in general, even though it was really heavy, it felt really good to go out on a date and be completely honest with someone about my baggage and not being rejected for it. Making this a positive experience at least for that.

ETA: Thank you all, I’m going to listen to my gut on this one and stop trying to rationalize it to myself by explaining away a huge red flag because I’m lonely. FYI: Gut reaction was “NOPE, NOPE, NOPE, NOPE, NOPE.”