Single Guys, Here's How to Flirt Without Being Creepy

Kelly E.

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Have dating apps and online interactions killed flirting? Or is it a social skill we can learn?

Last year, I became single for the first time in 18 years. I’m back in another serious relationship now but, before I landed here, I had six months in the dating world.

Here’s what I learnt:

People have forgotten how to flirt.

I didn’t intentionally set out to find guys. I was planning on staying single for a while at least. I didn’t go online to date, or “put myself out there”.

Pretty much as soon as I was single though, in fact: even slightly before, guys started asking me out. In various forms of “out”. I have to let you know here that I’m not especially stunning or above average, so I was quite shocked by this. Especially since they ranged in age from 19 to 50!

I turned most of them down (especially the guy who asked when I was still married — seriously!) but it quickly became obvious people have forgotten how to flirt properly.

Does this pass as flirting now?

This was some of what I was dealing with. I think you’ll see what I mean.

1. Young, cute but so-forward-he's-scary guy:

“What are you doing this afternoon? I could book a motel spa for us. I’m really discrete.”

Many guys online and in real life make the mistake of coming on strong too soon. I'd barely talked with this guy and he was booking a motel already? Slow it down. Flirting is a long game.

2. Desperately emotional I-can’t-believe-I’m-still-single older guy

Text message at 2am: “Are you still awake? I just want someone to spoon. It's been so long.”

Desperation never looks good for girls or guys. Confidence is attractive so even if you are desperate to spoon or find a partner, don't let on.

3. Sweet but slightly deluded player

After a second date: “I think we should do this maybe a couple more times.”

Seriously guys? This is the best you have? This is your game plan? No, no and no. Telling a girl you only plan to see her a few times is honest, but don't expect her to want to see you again.

I mentioned this pattern to my female friends in their twenties. They said they have no idea how to flirt either.

“If I really like a guy I can hardly talk to them,” one of my very attractive friends said.

Have Dating Apps Meant we Don’t Need to Flirt?

Is this why? I thought it was just flirting in person that we’d lost, but from my female friends' stories about online dating it seems to be an issue there too.

When you talk with someone online it’s different than meeting a stranger. You’ve at least established that you’re slightly interested in each other. There’s no guessing or reading body language needed. It explains the forward-ness women are encountering in dating. In some ways it can be refreshing to get straight to the point. One guy, after having a nice conversation in a bar, just reached out and interlaced his fingers with mine.

“I thought I should make my intentions clear,” he said when I gave him a surprised look. Yes, pretty clear!

In some ways that saves a lot of mucking around and wasting each other’s time. You’re either into it, or you’re not. Still, there was a part of me that really wanted a guy to woo me. (Such an old fashioned idea!)

And a number of women agree with me. We want flirting to be slower and gentler and, just…not so intense.

What women want

To catch her eye across the room and hold it for a bit (not gape in a predatory way.)

A smile. And if she smiles back, come over and chat. Make her laugh.

Take your time and let her know (with your great listening skills) you actually want to get to know her. Enjoy each other’s company. Hold her gaze sometimes, just enough to make her feel beautiful. Maybe offer to buy her a drink.

Watch her body language--is she's into you too or trying to get away?

Stand close enough, side-by-side, to hear each other talk over the music. Close enough for her to brush up against you accidentally if she wants to. If she's still smiling, lean into her ear and say something, so she can feel that tingle across her neck and lose her breath for a second. If she touches your arm, she's probably flirting back.

Introduce her to your friends and include her in your conversations.

When it's time to leave, offer to exchange numbers. If she's still interested, kiss her cheek. Tell her it was great to meet her.

When a guy flirted with me like that, that’s the guy I said yes to. And a year later I said yes when he proposed. He was cool and gentle, not at all forward, (even a bit nervous) and it was perfect.

That's how real flirting works.

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