I think you need to learn not to be in your head all the time. Such instances where you say you "ran out of things to say" "over-analysing" (I was/am guilty of). I've seen in some of your posts that you almost come up with excuses for a) not approaching b) not going out. Whilst some reasons are fair i.e. illness, just remember that you need to stop yourself from giving in to those excuses or else it will become a pattern, break the trend, go out when your ill, meeting someone and having a good time would probably make you feel better anyway.

Your post today about the girl on the bench, if I was in your position when she said "I'm with someone" I wouldn't have stopped the conversation (she was opening up to you a little) and exited because I assumed she had a boyfriend, she was showing you resistance to see how you'd respond. And even if she has a boyfriend, can a girl not make new friends? - Don't exit immediately when confronted with slight resistance.

The silence between comments is your friend. I remember 1 of the first dates I went on after hearing that silences between talking is fine. I basically took this girl on a walk and a drink after. During the walk we'd be talking, random stuff, thinking about it I think she was a dedicated animal/environmental lover so god knows what we were talking about. Anyway, I decided that I would pause and count 5 seconds in my head, then initiate conversation again, increasing the seconds and also decreasing. It added more tension and suspense to the conversation, gave her mind a little time to wander.

Other's might think differently but for the way I approach things, my personality etc... the silence is great.


Like your challenging progression, also try to counteract slight resistance, what's the worst that can happen?