8 Things That Will Make a Man More Likely to Flirt with You

Surprising tips, from dressing casual to flying solo, that will make men want to chat you up.

Yesterday, I was flirted with again.

In the early afternoon, the circuits in my apartment blew. That has never happened before, so I didn't know how to turn them back on and my landlord wasn't around. So, while I usually stay CHAINED to my desk from 9-to-whenever, in the hopes of getting as much work done as humanly possible, I had no choice but to spend the rest of the day elsewhere. As I prepared to go out, I dressed for comfort rather than attractiveness — very short black shorts (that probably showed a little back-thigh cellulite though I try not to think about it) and a black T-shirt.

I arrived at my go-to coffee shop only to discover that one of its A/C units was busted, making the place distinctly Inferno-esque. Cranky, I was making my way to another café when I passed a groovy little bakery I'd never paid much attention to before. The place had a few lovely little tables set up — all of them empty. I asked the pink-cheeked young man behind the counter — who couldn't have been much more than 23 — if it was okay for me to get tea and a sandwich and camp out for a few hours. With a sweep of his arms, he said, "Please! Be my guest."

So camp out I did. I decided to stay off the Interweb for a while, in order to concentrate better — and I worked, worked, worked away, feeling increasingly delighted with the progress I was able to make. When The Talking Heads came on the stereo, I bopped my head and tapped my feet a little, invigorated.

At some point, a goateed customer came in — another young man who also probably wasn't much more than 23 — and got himself a cupcake and some coffee. He sat down at the table in front of me and sat facing me, rather than facing the windows that looked out on the street. I thought that was unusual. But I didn't pay him too much attention.

Who knows how much time had passed — 15 minutes? 20? — before he packed up his stuff, came over to me, and said, "Are you having fun with what you're working on?" And I said, "I am! It's really coming along." Then he said, "Well, awesome. I could tell you were really digging whatever you were doing. In fact, I was even going to buy you a cupcake, but then I figured if you'd wanted one, you'd have gotten it yourself."

I smiled, and thanked him for the kind intentions, and there was some awkward additional mumbling between us before he shook my hand and left.

I'd probably been there about three hours by then, and the place had been bustling the whole time. But maybe 10 minutes later, things got quiet — the place was empty except for me and a couple of other customers sitting in the window seat — and the kid behind the counter said, "Are you being productive? It looks like you are." And then we got into a chat.

Based on all this — and similar life experiences in the past — I'd like to share some observations.


1. Dressing down. I will swear on a copy of War and Peace that I am flirted with far more often when I am dressed like a complete schlub, as opposed to when I'm dressed to the nines. The only thing I can conclude is that men are less intimidated by casually dressed women. I've also noticed that when I'm in my gym clothes, I almost never get chatted up — except by sleazeballs — and maybe that's because my tight spandex pants might actually be fairly sexy.

2. Being out in public solo. Much less scary to approach a girl who is by herself than someone surrounded by friends.

3. Seeming approachable without seeming desperate for human contact. It's very unattractive to be the person in the coffee shop who is making eye contact with EVERYONE. Even worse: Being the crazy lady who tells every single last person who walks in the door that they should try the Chai Latte Double Skim Milkshake Extravaganza — or asking every male with opposable thumbs if he can help you with your computer. Looking around you now and then is fine; smiling — especially at babies or children — is perfectly acceptable. But being Ms. Chatty Cathy isn't going to work in your favor.

4. Being out in a place that's just right: not intimidating or too crowded — or too empty. I think part of the reason Mr. Goatee felt so comfy talking to me is because the place we were in was so low-key and comfortable. There were people around — a group of three people was placing their orders — so it wasn't as awkward as it could've been if it was just the two of us and the counterman. But it also wasn't so packed that Mr. Goatee was risking failure in front of millions of people. (Or, like, 20). As such, small coffee shops, juice joints, bookstores with adjoining lounges, and libraries often encourage flirtatious behavior.

5. Being planted in one place. Moving targets are hard to approach. But if you sit in one place for a while, a guy can observe you long enough to become interested, accumulate his courage, and psych himself up to approach. But if you only stay still long enough to check your BlackBerry, he won't have enough time to prepare. Similarly, if you're always bouncing up and down to take a phone call outside — or running to the bathroom every five minutes — all that movement could scare him away.

6. Being really into whatever you're doing. It's human nature: When we see another person having a good time, we become curious about what's making him or her so happy. Also, for most of us, happy people are simply more appealing than unhappy people.

7. Creating a little something called "mimetic desire." When one man sees another man flirting with you — as Mr. Counterman saw Mr. Goatee — it gets his testosterone pumping. He says to himself, Why was that dude flirting with that chick? Because she seems happy with what she's doing, and she likes music, and she's kind of sweet. Of COURSE, he likes her. She's likable! In other words, when one guy sees another flirting with you (or simply talking with you), he takes it as a given that you are flirtation-worthy, and then he comes up with his own reasons to support that conclusion.

8. Having no expectations. This is the hardest part. And I really HATE to give such annoying advice — because how are you supposed to carry it out? But I SWEAR, when I go out hoping I'll meet someone, I never meet anyone. When I work too hard at a conversation that someone else has instigated, it always falls flat. Yesterday, I was really focused on my work; I wasn't thinking about boys. My attitude was: Eh, there will be no flirting for me today, because I'm just not a hot mama at the moment — I was dressed down, hanging out in a fairly unsexy place on an uncomfortably hot and very unsexy day. Also, although the two coffee shop dudes were cute, they both just seemed so young, even for me — both could still have been in college, from the looks of things — that I just assumed I was out of their normal age range.

I know it's hard not to be too interested in a certain outcome — on having a guy approach you and ask for your digits or whatever. But the less you think about it, the better. Focus on things that are in your control — like your work — and you'll be better off.