moishy asked for “interesting and/or funny stories”. Funny Shidduch Stories is a subset of interesting and/or funny stories.
I felt that if he wants to have a good laugh while waiting for others to post interesting and/or funny stories he could start there.
Here’s one-
One Erev Shabbos, my brothers and I went to visit a former neighbor who was not Frum and wasn’t doing to well physically. He had recently moved to an upscale non-frum neighborhood and they weren’t used to seeing Frum people around.
After we wished him a Gut Shabbos and left a neighbor came running out of his house and said “were you just here for Steve?” after we nodded yes he started crying, “I can’t believe it, I just saw him and he looked so good, I can’t imagine how it happened so fast, oy, his poor wife and kids…”. We had no idea what he was talking about until he asked where the hearse is.
We then realized that there is only one time when he sees frum people in suits. He then warned us that if we ever pull that prank again we had better be wearing ties with Mickey Mouse on it so that he knows we are not the real ones.