Reply To: Dating Someone You’ve Already Dated

Thanks for all the answers, I’ll probably think about it for a while longer but assuming I decide to try it again, I have a small point I’m not sure about.

I know there’s a thin line between going with your gut and being a creep, so I figure I should not contact her directly. On the other hand I feel like if I just had a shaddchan ask her if she wants to go out again without being able to explain my reasoning there’s no reason to think that she would say yes. If there’s one thing I learned from this it’s that the more people involved in a shidduch the more confused everyone gets. Would it make sense to ask the shaddchan to see if it would be ok to send her a message via email or something like that?