I’ve been wanting to set up my brother in law with my good friend since he went to Eretz Yisroel a year and half before they started dating bu of xourse it wasn’t even looked at since he was totally not in shidduchim. For that entire time until he came back I brought up the idea to my mother in law every time I spoke to her (quite often) until I finally said “there’s no one else he can marry besides for her!” That did it! They went out a few time and hit it off even better than I could’ve imagined! They are happily married now!