Hmm, LU says “However, there are cases in which both of these are seriously problematic.”, etc
1. Why is it problematic is a boy and girl meet on their own? The majority of the previous generatio did just that – at college, homowack, grossingers, sky rink, etc.
If the parents are OK with it, why would you need to launder it thru a shadchan? Because the neighbors will talk? WHO CARES what the yentas say?
2. You said its problematic to go out with an OTD boy. He is not OTD anymore, he made a comeback. Give him some credit. If you always consider him to be OTD, it will just push him away again.
Chag Kasher Ve’Sameach.