I personally don’t like the idea of dating more than one person at a time (can you decide which song or food you like better by listening to them or eating them both at the same time?) but it’s just my opinion.
This story happened to my sister (who shares my opinion). My only involvement was that I was an unknowing accomplice.
A shadchan called and had a guy for my sister who (at that time) was the top guy in Lakewood. Guy drives in, takes her out and she decides she isn’t interested. Before she can get in touch with the shadchan- another shadchan called to set her up with the top guy in Lakewood (it must have been a tie for that zman). My sister readily agreed to go out with him. This guy though insisted that my sister travel to Lakewood for the date.
When she called the first shadchan to let her know her decision, the shadchan told her that she has to go out with him again since it’s understood that if he has a long drive he gets at least two dates.
She is now committed to going out with two guys.
She told the first shadchan that she has to go to Lakewood for a simcha or something so she’ll go out with the first guy in Lakewood.
My mother got all frantic that she might come back a little late from the first date and the second guy will be sitting in his car watching her come back from a date so she had my sister go out from two different cousins houses.
Now here’s where I come in. My mother called a cousin of ours and asked them to invite us under the guise that my wife needed a break (she was in her 9th month at the time). So while we were in Lakewood my sister “happened to also be there” and needed a ride from one cousin to another for a date. (I only found out about the whole story after the fact.)
I guess it’s better to say that your brother dropped you off for the date than to say that another date dropped you off!
You all probably figured out what happened next, right? She liked the first guy better and agreed to go out with him again. When my mother called the shadchan for the second guy, the shadchan told her that she made him commit to two dates since my sister was traveling for the date.
Now again she had to date two guys, in the same city on the same day.
After this date she liked the second guy better and ended it with the first.
She later ended it with the second guy also. 🙁