No, seriously, I wasn't able to hold an interesting conversation. Sure, I could discuss the morning's sugya, or that time I was m'kavein to the Maharsha (the high water mark of Yeshivah for me), but nothing to hold a girl's attention.
It was a measure of my emotional immaturity and lack of self-esteem that I couldn't find anything relating to someone else or even the rest of the world to talk about. I was shut off from and afraid of the world. It took months and a string of first dates to bring that home to me.
I remember going back to the shadchan who set me up with the one girl who had agreed to a second date, long after the event, and asking her if she remembered why the girl didn't want to see me any further. She politely told me she didn't remember that far back, and, smiling, couldn't herself think of anything that might have turned her off. But after running out of fingers counting first dates there was obviously something wrong. With me. Depressing, no?
In hindsight I was always depressed. A sort of low-grade depression stemming from that explains my behaviour and thinking all through school to the present. Withdrawn, quiet, introverted to the point of anti-social. Living in my head. It was safer than outside it.
This wasn't the trigger that threw me into full-scale, non-functioning depression. That came later. I needed something more... How about proposing to an emotionally troubled schoolgirl about ten years younger than me and then breaking it off? Would that work? It did.