Dear Girl I Went on Three Dates With,

I am writing to let you know that it doesn't have to be awkward between us. I know people always think it has to be weird when they see each other again after ending it, and it might just be that way the first or second times, but trust me, I think we will both go on to live long fulfilling lives, just not with each other. 

The shadchun described you to a tee, “down to earth, cool, religious”, all the qualities I am (still) looking for, and I appreciated how you become more chilled out on our second and third dates. I liked how you wore sneakers and a jean skirt on the third date and I hope you appreciated my untucked shirt (under my zipper sweater) and ordering a gin & tonic with dinner. But to be honest, our dates were more like gin & platonic, and I think we both deserve something stronger than that.  We can use excuses like different hashkafas, sense of humor, goals or family values, but when it comes down to it we broke up because I  was not into it (enough to break my shomer negia for).

Don't take that the wrong way. Do you ever get that feeling that you are embarrassed to be out on a date with someone and hope to Hashem that you don't see anyone you know? You will be proud to know that I never once felt that with you. I am glad we got to play basketball at ESPN Zone and share our year in Israel stories and commiserate about how frummies are so fake. That was fun. I didn't even mind that it took you 20 minutes to come down to the Brookdale lobby on our first date and asking to pay for half of the bill at dinner was very modernish. But nisht a turn on.

I meant it when I said I wanted to stay in touch and be friends, at least until I go out on my next date, which is next week. And if you know her I hope you say good things, but don't let her know where we went on our first date cause if you want to know a secret, (I take all my first dates there. Shh. )

I hope we can always stay as “someone I went on 3 dates withs” forever.

Hatzlacha,
Guy you went on three dates with