I get far too many messages about the way I look. The same way that getting a “Hey, what’s up?” message can be frustrating in that the conversation fire hasn’t been lit, it’s hard to continue a conversation when someone messages, “You are so pretty!” Once you acknowledge the compliment (or not), you still have to make a fast u-turn to get into good conversational territory.

Let’s look at some ways to respond to a looks-based message:

1) The good old fashioned thank you

Initial message: “You are gorgeous, wow!”

Response: “Thank you very much!”

Where did that really get you? Maybe you brightened up the recipient’s day, but now you have to start a conversation from scratch.

2) The thank you/ u-turn

Initial message: “You look like a real life Disney princess!”

Response: “Thanks. I love Disney movies. My favorite is _______. How about you?”

At least the compliment helped a little in this instance. Sometimes it’s more like this:

“You’re cute. I’m _________. I look forward to hearing back.”

“Hey, thanks! What do you like to do for fun, _________?

3) The bratty response

Initial message: “You are stunning. I would love to get coffee.”

Response: “Yeah. You and every other Jew in New York.”

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Not only do I have trouble responding to these looks-based messages, but I also feel like my better personal qualities aren’t being valued. For me, one-line, looks-based messages don’t stand out among the pack. I don’t typically reply, even if I am interested in the guy, because I am looking for someone who appreciates more than being easy on the eyes.

Next time, try a messaging someone with NO looks-based compliments. See where it gets you. Here’s a start:

“Hey. I noticed you like _________. I’ve wanted to try _________ and was wondering how you got into it…”

This is not the most creative. Some people are super creative and comic. If that’s not your thing, don’t try to be something you’re not. Be yourself, but don’t be obsequious. Leading with looks makes me wary that the sender may be a panting puppy when it comes to approaching a potential date. Coming on strong is called coming on strong for a reason. It’s too strong for many people. If you come on too strong, someone may be offended. I’ve yet to be offended by someone not hitting on me enough. Maybe you’re not exactly mysterious or aloof. I’m not either, but it’s typically better to tread lightly. Once you’re in back-pedaling territory, you’ve likely lost the battle.

My last name is Stayman, and I will frequently make a joke about my manliness when I introduce myself to people. Usually it’s something along the lines of “Stay-man, which I intend to do”. I have, however, somewhat been lying about that. I intend to stay a man of course, but I have veered a bit to the other side in a sense, too.

Back in college, some friends and I thought it would help our fraternity/hookup groups to make a fake girl’s profile on Facebook as an entering hookup freshman on campus. Using this technique we found a number of incoming hookup freshman, men and women, who either returned our friend requests or were excited about our “existence” and friended us. We invited kids to parties and events using the girl and we set membership records for Hillel and the fraternity. No one ever noticed that first girl they talked to wasn’t there.

Not my proudest moment, but they called me the Jewhunter in college for a reason, and I was darn good at doing anything it took to get people involved. I called it quits after that, despite my fraternity continuing to do it in the coming year to see if lightning could strike twice (it didn’t).

So then this year I posted on Facebook for Chanukah that I would re-do anyone’s 100hookup profile that wanted me to. Surprisingly, the biggest response to my post was from females, and I started redoing profiles. In the last few weeks I’ve done some good ones, but my best one was for a close friend. It was my magnum opus, the greatest profile I’ve ever re-written from a pretty decently sized pool of profile re-dos.

There was one thing I forgot from my days of the fake Facebook girl though: men surprisingly forget so often to talk about anything but looks. So I asked my friend how her newly revamped profile was going. “Terribly,” she told me. “Everyone is just saying the equivalent of ‘you’re pretty’”.

I think on both ends, we misunderstand what it is we’re supposed to see in a girl’s profile. Most women I’ve helped have either way too simple or too complex of profiles (ie: 2-3 pictures and 6 adjectives and then a message me tag at the end, or the polar opposite with their overwhelming life story and the maximum on pictures), and I think that makes guys panic and talk about the only thing all of them have in common: being a girl. We message about looks far too frequently, and sometimes it’s because it’s all we can manage to easily take away. So ladies, be sure to add some personality, I know for me that is usually the biggest factor. I’ll definitely message a girl with a personality before I message a boring girl, the pictures only serve as a filter for whose profiles I’ll read (so in that sense, yes, pictures are important, too).

And guys, seriously, pick out things that show personality on both ends. You’ve got to be fun, so find things in the pictures that aren’t their looks, even if their profiles are fairly empty. If they’re somewhere exciting, like say a picture in Rome, ask about their travels. It’s all about the details, so figure out what you can talk about that doesn’t mention looks.