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.

There are certain things that are not to be shared on a first date. If it has to do with sex, drugs, or any other illicit activity, then hold off… maybe forever. Lots of things fall under the sex category, including nudity, number of partners, pornography, strippers and so on. Anything along those lines should be considered over-sharing. Drugs include both the prescription kind as well as the illegal kind. No one needs to know about that on a first date! Money, why past relationships ended, and anything having to do with drama can wait for another date.

First date topics should start with continuing the email conversations you began, which usually address your commonalities. Just let it flow naturally from there. If you find the rapport waning, then revert to asking questions from the 100hookup profile. “Remind me again where you went to school/where you grew up/what you do for a living/how many siblings you have?” Those are always easy ways to get the conversation going again.

We’ve all been there. You meet someone new, you get a name, and you think to yourself “what would get a conversation rolling?” It probably occurs to you that people like talking about themselves, and what could people love more than their job? So you ask it: “What do you do for a living?”

I’ll let you in on a secret. Some people like that question, but a lot of people see it for the conversational crutch it really is. Asking “what do you do?” is a faux pas in a few ways. For starters, you’re assuming all people like their job, and sadly that is not the case. I know when I was working retail I told very funny stories about things that happened to me (like a river of urine I found in my store), but it was the last thing I wanted to associate with new friends. Secondly, some people may take it as you trying to gauge how much money they make. And lastly, sometimes people just want work to stay at work.

When this question comes up, some friends and I have vowed not to reveal our jobs within thirty minutes of first meeting someone. We’ll say ridiculous jobs like bounty hunter, fruit bowl modeler, or selfie coach, and move the conversation along. So in order to help others make a more fun, lasting connection with a new friend, here are my three alternative suggestions for that rut when you need something to say:

1. Talk about what’s around you. One of my favorite social rules is called “Observe, Share, Ask.” You see something in a room, mention something about it and how you relate, and ask something about the other person’s experience. For example, if I was in a room and saw a picture of a clown, I would say something along the lines of “did you see that clown picture? The circus always terrified me, did you ever like it?” This allows me to share a bit about me while sharing an experience (we both see the picture), and allows the other person to open up about their experiences.
2. Ask how they got there. Whether you’re at a party, synagogue, or a singles mixer, ask someone who they know or how they found the place. This allows you to find mutual friends (this was my usual conversation starter at parties in college), and build a connection about any hooks that are revealed — they could be classmates, fellow natives, or mutual friends.
3. Ask what they do in a different way. This is a fun one to me in that you still get to ask the job question — if they want to talk about it. An article I found on LinkedIn a while back had the amazing option of asking “What keeps you busy?” This is such an amusingly vague and open question that people can answer with anything from, “I blog for 100hookup and collect beer glasses” to what they do for a living.

Hopefully this sparks your conversations a bit, feel free to leave other ideas in the comments!