There is a raging debate in the shidduch world that has been commented upon by many. The sides break down like this:
Side A: If you send a picture with your shidduch resume you are a slut/manwhore who is trying to get people to date you using your looks which is the opposite of the Torah and if you want to see a picture you are clearly only dating for eventual sexual gratification and I don't want you anywhere near my friend/child/student. If you own a picture of yourself I hope you like hot weather because you are going to hell. Selfies that you send your telehealth dermatologist also count.
Side B: You expect me or my child/friend/student to go on a date without knowing if the person they are going out with is their type? Heresy! The torah says that a couple should be attracted to each other so sending a resume without a picture is an aveirah that warrants kareis. Besides, we all know that if you don't send a picture you're clearly trying to hide some horrifying physical flaw.
Before I started dating I went to a shiur about shidduchim where the Rabbi said that you should absolutely never date a guy who asked for your picture. Adorable, pre-dating me was like "yeah!" That lasted about 2 dates. Everyone wants a picture, whether it's the guy, the guy's mom, or the shadchan who's trying to keep the thousands of singles straight.
Everything about the picture tends to get so dramatic. One shadchan would only accept my resume if my picture was on the resume because she didn't have time to look through two documents. Others won't accept a resume with a picture on it at all.
Then there's the picture itself.
I've been told my picture is "too yeshivish." That's weird because my picture has never learned a page of chumash #dadjoke. The last time I had a professional picture taken of me was at my brother's bar mitzvah. I love this picture, it makes my hair look fantastic. The bottom of the dress I was wearing was gold and the top was black. In the picture all you can see is the black top and not that the gold is straining within an inch of its life to push my boobs as high as they will go. Therefore, because I am wearing black and have nice hair, my picture is "too yeshivish"
I have also been told that guys want a relaxed picture. The problem is that all my selfies of me in bed (that I take when my mom asks "how was your day" and I respond with "haven't left my most favorite place") aren't exactly flattering. I think this is like that OneDirection song "That's What Makes You Beautiful" and Amy Schumer's excellent parody of it. In the parody the members of 1D tell Amy to take off her makeup because she's already beautiful. She does that and they are horrified. Why does she suddenly have acne scars, bags under her eyes and frown lines? Because guys think makeup means "red lipstick' and nothing else. When guys ask for a more relaxed picture its worse than asking for a formal picture because at least at a simcha you were prepared to be dressed nicely. Now these guys want to see you in full hair and makeup, but, like, at the beach. And I do not wear makeup on vacation.
Sometimes I will realize that the picture I am sending out it quite old. When I graduated college I decided it was time to stop using my high school graduation picture as four years had passed since I had it taken. I updated a shadchan with the new picture and she reached out to tell me my old picture was better and I should stick with that one.
Shadchan, I would also like to always look like I'm 18 and don't know what a deductible is but at a certain point that is a flat out lie.
A lot of guys like to send pictures where they are holding their niece/nephew in a funny way to show that they are good with children. The problem is its hard to filter out these from the pictures of divorced 40 year olds with actual children who hit on me for free babysitting.
Cropping isn't a good look. I know it, everyone else knows it. But sometimes you take loads of individual pictures that all look stupid and the one that looks good has your stupid brother/sister/friend/celebrity in it. So you crop.
Is it a flex to have my shidduch picture be my selfie with Daniel Radcliffe or does that just set me up for failure?
I've actually been on a few dates where the guy hasn't had a Facebook or Linkedin so I can find out what he looks like. It's a little weird not knowing a thing about his face beforehand but either way you get the free food. In these situations it is important to ascertain that he actually is your date and not an uber waiting to take your neighbor to the airport. You can tell because the uber driver will open the door for you and the date will just say something like "I'm parked illegally let's go!"
I don't think it's horrible to ask for a picture and I don't think it's horrible not to. I do think that people should accept whatever I've given them and try not to judge me too harshly on the fact that I'm wearing black or the picture is cropped.
Judge me for something real like how I start off our first phone call with "so where are you taking me to eat?"