This might not count as a shidduch story but it’s funny
Many years ago in a shtetel somewhere in Europe, there was a girl named zissel who unlike most girls behaved in a very immodest way and openly flirted with bocherim.
There were two bocherim that fell for her flirting and bird for her hand in marriage, zissel wasn’t the type to ask advice from a Rov, but in this case she did, sincerely or disingenuously she approached the Rov and asked “Rabbi, there are two bocherim who want to marry me, Chatzkel and Berish, tell me Rabbi which one is the lucky one which one will marry me?”.
The Rov replies, “zissel, I will be very honest with you, Berish is the one who will marry you but Chatzkel is the lucky one…”