It Takes Two People to Flirt

How to up your game

I love flirting. Talking to a new person makes me a bit nervous, but flirting has a fun energy to it.

Getting to know someone and figuring out whether it can go somewhere is exciting. Flirting is a great way to lay the groundwork for that exploration, see if there’s a connection, and maybe build one if there isn’t.

Plus, I’m a big fan of anticipation when it comes to arousal and sex, and flirting is all about concentrating and channeling that anticipation.

When my social anxiety doesn’t get in the way, I tend to be a naturally flirty person. I’m also an overly friendly person, and because of that I can give off slightly flirty vibes if I like someone and I get the sense that they like me too.

Because of that, I have a lot of practice with flirting, and I consider myself a decent flirt.

These days, I flirt digitally. Unless you count Mr. Austin, I haven’t flirted with anyone in person in a very long time, and people don’t flirt with me in person often, either. (Being surrounded by kids and a husband makes me look off-limits.)

Online, it’s a whole other story. I write about sex, about being polyamorous, and I also give off a little mystery by not sharing my photo. That’s a recipe for being hit up every once in a while.

Sometimes, I’m not feeling it at all and I’ll just ignore it or politely decline. But sometimes I’m game so I’ll respond. Even when I’m game, that game doesn’t often go very far. There’s a brief flirty exchange, but it fizzles out quickly. I struggle to keep up with my end of it, and it just feels more frustrating than exciting.

My first assumption is always that the other person just isn’t that interested in me. They’re just not feeling it but they’re looking for a polite way to back out. So, I always make sure to give them opportunities to bow out, or I’ll even bow out myself. But in a lot of cases, they keep showing interest.

They’re still trying to flirt, but something about the way they do it isn’t working. It feels like they’re initiating a flirty exchange but have no follow-through.

I’ve been thinking about this lately and asking myself what it takes to flirt well, and what happens when flirting falls flat.

You Can’t Flirt if You’re Not Given Anything to Work With

It’s really, really hard to flirt with someone who seems to be keen on it but isn’t giving you enough material to work with.

Things can start really well — promising, even. But if you don’t keep learning new things about them, it’s going to feel one-sided and it will feel more effortful than it should.

That happened when I started flirting with a guy named Eli.

I don’t often flirt with complete strangers, but I once put an ad on an r4r subreddit and started talking to a few people.

I got a mini flood of responses (the male to female ratio in those places is really skewed) and I wrote back to the men and women who managed to get my attention and who wrote something I could use to keep the conversation going — they made a couple of cute comments about things I wrote in my ad, they told me something interesting about themselves, or they made a decent joke or two.

Eli didn’t give me a ton of material up front. It was barely enough, honestly, but he was really cute and had a nice beard (I’m only human).

He seemed interested in me, but every time we exchanged emails, I felt like we hit a dead end.

Every day he would ask me how I was doing or if I had any plans. When I answered those questions, he’d reply with something like “Haha, that’s cool.”

That didn’t give me a lot to follow up on.

I tried drawing things out of him by asking him questions. That wasn’t much better. When I asked him what he had been up to lately, what he has planned, or if anything interesting was going on in his life, he’d write something like “Oh, not much.”

We were getting nowhere, so I decided to let it just fizzle out. But then he’d come back again. And again. And again. Each time, with almost nothing to contribute to our conversation.

Trying to flirt with him felt like a chore. I was a little interested in him at first (well, his photo anyway), but not enough to literally carry the entire conversation in every single interaction with him.

You Need Opportunities to Contribute, Too

There are other times when someone I was flirting with was giving me lots to work with — they were open books, they would answer all my questions, and show me every side of themselves — but it didn’t work because they didn’t bother getting to know much about me.

If I’m going to flirt, the person I’m talking to needs to give me something I can bounce back at them. But it’s a two-way street — they need to take what I give them and bounce it back at me, too.

That’s what happened with me and Rob. Things with Rob were fun and promising. I really liked him and things would sometimes get hot. But I found it really difficult to flirt consistently with him.

I was getting all the material I needed. I asked about him a lot and he liked to talk about himself, so I had an arsenal of little details I could lean on. But I was still struggling because it wasn’t always reciprocated.

He didn’t ask much about me, and he really didn’t seem all that interested in me unless it was related to sex. He just didn’t seem curious about me at all. When I volunteered information, it sometimes felt like he didn’t care, and when I said things that could easily invite questioning, he never bothered following up on them.

He didn’t have a lot of material to work with and it showed. Other than describing what he’d like to do in bed, he didn’t manage to do much flirting.

After a while, that got a bit dull. Flirting is most fun when both people are really engaged. Getting so little from his end didn’t make flirting exciting — it just made me wonder why I was giving him my A-game when he was giving so little back.

You Can’t Rely on Compliments

Sometimes, I find myself flirting with someone whose idea of flirting is to lavish me with compliments.

It’s sweet. I appreciate compliments, even if I sometimes have a hard time taking them seriously.

And I know it comes from a well-intentioned place (what better way to show someone you like them than by complimenting them?) That doesn’t change the fact that compliments alone can’t make someone a good flirt.

I’ve had a few guys try to hit on me by just complimenting me — telling me I look cute or that they find me attractive.

The problem with just giving compliments is that it gives me nowhere to go. It’s hard to base a conversation off compliments. I can compliment them back, and sometimes I do, but then I wonder when the actual conversation is going to start.

Flirting with only compliments is basically like starting off with a “Heyyy.” (And don’t get me started on Heyyy guys.)

It’s Not a Gender Thing

Although I’m a pansexual lady, I’ve had more experience flirting with men. So, they’re the ones who give me the most material when I’m trying to analyze flirting flubs.

But it’s not a gender thing. Women are just as guilty of not bringing the heat.

Some of the women I found myself talking to just didn’t seem to know how to bring much to the table. They didn’t tell me much about themselves (even when I asked) or didn’t seem comfortable asking me anything.

One woman who reached out to me online wasn’t passive at all. She moved fast as hell. And I mean move — the girl was uHauling hard and I’m surprised she didn’t ask me for my house key. There was no way to really flirt with her because she was basically trying to bypass the flirting stage (and the getting to know each other stage, and I have a feeling she would’ve skipped introductions if she could’ve).

And then there’s me. I’m not the worst flirt, but I am guilty of not giving up enough personal details to keep a good back-and-forth going.

I get nervous, I feel too shy, my social anxiety takes over, or I’m intimidated by the person I’m flirting with. Any of those can make me bomb hard. Especially if I really like them.

I may have excuses or explanations for why I fuck up, but it doesn’t matter — it’s still bad flirting. That’s a small part of why I’m trying to overcome my shyness and anxiety. I want to up my game. Because contrary to what some people have told me, I don’t believe that it’s all up to men to carry a date or a conversation.

How to Flirt Well (Even if You’re Not Incredibly Charming)

I’m not a pickup artist or a dating coach, but I’ve learned a few things from being on the receiving end of bad flirting and having kicked myself for my own flirting fuck-ups.

I would be surprised if most people are naturally good at flirting, but that doesn’t mean everyone is hopeless. Having the right approach matters more than having natural charm.

If you’re struggling with your game, here are a few things you should work on.

Ask Questions and Pay Attention

When someone’s flirting with you, you want them to feel like they’re responding to you, not just talking at you.

You want to be able to do the same. And you can only do that if you’re actually getting to know the person you’re talking to.

I know that asking questions and paying attention sound basic, but I’ve been surprised at how often it doesn’t happen. That includes me, too. Sometimes, I get so flustered I don’t realize I’m not doing my part in a conversation.

One of the best things about getting and retaining lots of little details about someone is that you can refer to them again later. I love a good callback in standup comedy and in personal essays. They also work really well when you’re flirting.

A callback shows that you’re interested and attentive. It makes the other person feel heard and it catches them off guard. Done well, it also shows that you’re considerate or witty.

I also love creating new inside jokes when I’m starting to get to know someone. They’re a really good way to spark a connection and create some speedy intimacy, but they only work if you’re really paying attention to what the other person is saying.

You can’t go wrong by paying attention and getting to know more information about someone (plus, it’s a good way to make sure there are no red flags). The only risk is overdoing it by doing a little too much background research on the person you’re talking to.

Make it a point to only work with what they’ve given you. Referring back to something they said to you or maybe something they posted to social media the day before is safe territory. Digging deep and making a reference to something they posted eight months before meeting you will give off too much of a stalkery vibe — instead of smiling at your callback, they’re more likely to wonder “Wait. How the hell does she know that?”

Doing that much digging also creates an imbalance. When you make someone feel like you know a lot about them but they know almost nothing about you, it makes flirting awkward. That’s why I don’t usually flirt with my readers — I don’t know them enough to flirt effectively, and there’s not much left for them to discover about me.

Volunteer Information About Yourself

Asking too many questions can be a problem, too. If you’re not volunteering information about yourself, the person you’re flirting with is going to have a harder time saying sweet, suggestive, or slightly intimate things about you. And how can they gently tease you without having anything to joke about other than your appearance? (And you do not want someone teasing you about your appearance!)

And I do mean volunteer the information. If you’re only going to answer questions about yourself but won’t talk otherwise, they’ll feel like they’re carrying the entire conversation or that you’re just not that interested in revealing yourself to them.

This is another one you have to be careful not to overdo, though. A lot of people worry about being interesting on a date or when they’re casually flirting, so they talk about themselves a little too much. But being good at flirting isn’t just about being interesting — it’s also about being interested.

When you volunteer information, you should also do it without bragging. Bragging doesn’t create conversation, it closes it off. There’s nowhere to go with the conversation when someone’s bragging. You can either just agree or you can get into some one-upmanship by doing some bragging of your own, but that doesn’t go anywhere but downhill.

Work on Your Conversational Skills

If the conversation isn’t flowing well, the flirting’s going to stall along with it. So, if you want to improve your game, you have to improve your ability to keep a conversation moving.

And conversation isn’t just talking — it’s a skill. A conversation isn’t something you just have with someone, it’s something you keep going.

One of the basic things you need to master is the number one rule of improv comedy. You have to “yes, and…” them. It’s remarkably easy to shut down a conversation even when you’re not trying to do it. You need to know how to answer questions, pose a question, or just generally talk in a way that invites more input from the person you’re talking to.

Don’t Make Anyone Feel Trapped

The hardest part about flirting is getting started. You’re basically putting feelers out to see if they’re interested in flirting with you and if your flirtatious comments are welcome.

One thing I’ve noticed is that a lot of people will go in too fast or too hard. And when they do, it makes me feel trapped. They’re putting me in a hard place of having to either flirt back or explicitly turn them down.

That’s a tough place to be in, and it doesn’t make anyone feel comfortable. It’s much better to be tentative, to open things up in a way that lets them gently back out. Doing that shows you can be trusted, that you’re respectful, and that it’s fine if they’re just not feeling it.

It’s all about making the person you’re flirting with feel more comfortable. If you give them an out, they’re more likely to stay in.

Don’t Get Discouraged

Everyone has screwed up when they were trying to flirt, and anyone can get better at flirting. Just because you struck out a few times doesn’t mean you should give up on dating or start posting on incel subreddits. You probably just need some more practice.

Look up some flirting tips (avoid Pickup Artist bullshit and anyone who promises that “you can take her home tonight!”) and analyze what went wrong after an awkward date. Tell your friends about it and pick everything apart so you can figure out what you could’ve done differently.

Yes, sometimes the other person just isn’t interested or they’re the one screwing up the flirting. But there are better and worse ways to handle that, and you can always learn something by going over things.

Whatever you do, don’t get discouraged if you’re struggling. You’ll get better!

Get Your Flirt On

There are a lot of potential flirting fails. And sometimes, two people just can’t click — no matter how hard you try, there’s just no chemistry.

But unless both of you show interest, share personal details, and bring the heat, you won’t even get far enough to know if there is a potential for a connection.

Flirting is reciprocal. You might be able to sustain some one-sided flirting for a little while. You might even manage to stay interested based on other factors (like a face you don’t want to look away from or the kind of tits you have to keep reminding yourself not to stare at). But you’ll never have that exciting, hot flirty energy.

There’s no better feeling than flirting that just flows, when it’s not an awkward struggle to make conversation. It’s the rush of getting to know someone along with the butterflies and blushes of having someone sweet talk you.

It’s worth doing and it’s worth doing well. So get out there and get your flirt on.

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