6 Cheesy Ways to Ask a Girl Out You Don’t Want to Repeat

When it comes to asking a girl out, there are a number of ways you can do it. The best way to go about it depends on a number of factors. You just don’t want to use any of these cheesy ways to ask a girl out.

One thing that’s true across the board is that cheesy pickup lines are a no-go. In exactly the right context they can be mildly amusing but for the most part, it’s nothing more than cringeworthy. At such an early stage in the relationship, demonstrating that you’re the cheesy type is heading in the wrong direction.

Cheesy ways to ask a girl out

Before we get into it, I want to make a quick but important distinction here. I support experimenting with the way you ask women out. Trying to use the same canned approach every time gets boring at best. At worst you’re potentially missing out on opportunities.

Consider these examples as the style to avoid but beyond that, get creative! Be that refreshingly different guy, it’ll turn out well for you in the long run.

With that out of the way, let’s take a look at the six most cheesy ways to ask a girl out. If you find yourself gravitating toward these options you really need to take some time to evaluate your skills. There are couple great books out there for helping you improve your overall skills and ability to attract women, especially your “inner game”.

The classic pickup lines

In some situations, it might be funny to use a pickup line once you already know each other. If you’re using it as part of your approach to asking a woman out, 99% of the time it’s pure cringe.

I’m talking about the classics like:

“You must be tired. You’ve been running through my head all night”

Or

“Do you have any raisins? How about a date?”

I’ll admit I did have a chuckle researching some of the classics for this article. At no point can I ever imagine using this with someone I haven’t met and expecting a positive outcome.

Instead, at this stage you’re so much better off just suggesting a date idea and time. Ultimately she doesn’t care about the words that you use to ask her out. Where you run into trouble is when you use an approach that paints you in a bad light — in this case with a hard cringe.

The humble brag

Hanging around some of the higher end bars, this is something I’ve heard far too often. It makes me physically uncomfortable every time I hear it. Granted, alcohol may be part of the reason but it’s so much more transparent than they realize.

In case you don’t know what I’m talking about, here are a couple of actual examples I’ve heard:

“[Yawn] wow, I am so tired. I had to be up super early this morning to take my Lamborghini in for its first service.”

and

“… that’s what my wealth management adviser tells me anyway. Once my net worth was over a million dollars I had to change how I looked at things. I reached that point years ago [smug chuckle].”

So bad.

The open brag

This is at least more honest than the humble brag but it’s still so hard to listen to. It’s just literally telling someone how great you are and expecting them to be impressed by it.

There’s something I noticed dealing with high net work individuals for work. The more successful/affluent they were, the more humble they were about it. Those in that mid-range liked to pretend by flashing their money around and telling people how much they had.

Maybe you are worth a million dollars and you should be proud . . . But do you really need to tell her straight off the bat?

Another actual example I overheard in a Sydney bar last year:

“I’m a major real estate investor down here so I have the funds. Someone as smokin’ hot as you, I’d happily take care of you for the rest of your life. You’d never have to work again [smirks and sips his drink].”

Having had the pleasure of being lined up behind them at the bar, I can confirm they didn’t know each other and he was serious. I can also confirm she got her free drink from him and disappeared into the crowd. Is there a lesson here?

For the most part, women who are receptive to this approach are probably not the type you want anyway. It’s easily one of the most cheesy ways to ask a girl out.

The pickup artist (PUA)

This is a controversial topic so let me point out my view on it before breaking it down a little more. The underlying notions covered in the pickup artist community are correct and valuable. The way they’re delivered and the way women are often looked at by that community are typically appalling. Assigned an arbitrary number on a 1-10 “HB (hot babe)” scale and discussed like a pawn on a chess board.

I’ll also say that the initial literature is generally OK. The issues come from how the vocal part of the community interpret and employ it. These poor interpretations make it a gold mine for cheesy ways to ask a girl out.

I don’t suggest that you stay clear of the guides and articles from that community. What I do suggest is that you read it for the underlying ideas but come up with your own delivery.

For example, “negging”. This is essentially a mild insult designed to undermine her confidence. This is meant to have her seek validation from you. There’s no disputing that it works with some women, my issue is that it’s kind of a dick move. Who are you to make her feel bad about herself so you can maybe get laid?

I digress. For this one, let’s take a look at a couple more real examples. The first is one I’ve heard at a bar nearby. The second is something sort of similar that I use from time to time escalating from Tinder to phone number.

The PUA: “I’m not usually into women so tall but you seem okay”

My approach: “You seem fun enough. Want to text me on [phone number] and we can plan something for later this week?”

At first glance this might seem quite similar. There are two important differences here. Firstly, the PUA approach is insulting by design. Mine is nothing more than me being cheeky. It’s not meant to be insulting.

To make sure it’s received as such, it’s only ever used on the back of a high energy, humor-filled conversation. Not once has someone taken offense to it.

The second key difference is the response it’s meant to elicit. The PUA approach often gets a negative or self-conscious response which sets up for negative conversation. On the other hand, the response I get is fun/funny. “Haha I’m good ENOUGH, huh? I can work with that”.

This type of distinction is exactly what I’m talking about. The “negging” concept does work. In my opinion, insulting women as part of your “game” is disgusting. It’s worth reading about to understand why it works then experimenting with your own, respectable version.

The rude demand

Being confident is so important when it comes to dating. This is a trait that seems to be universally attractive to women. There’s also a fine line between “very confident” and “arrogant” which can be easy to overstep.

Here’s another good vs bad example of what I’m talking about:

Bad

“Okay, we’re going to the new restaurant on 3rd tomorrow night. Just booked us a table at 8:00pm”

Good

“We should go to that new restaurant on 3rd tomorrow night. I’ll book us a table if you’re free at 8?”

While neither are weak, needy or lacking confidence, there’s still a huge and obvious difference here. Where the first just abruptly tells her what to do, the other makes a clear offer with an easy out if she isn’t interested.

It all comes down to respect. You owe each other nothing, the least you can do is ask rather than tell, right? Manners go a long way.

The constant pesterer

This one is probably quite clear from the heading. If you’ve extended an invitation to her on a number of occasions and she declines or cancels, it’s time to move on.

While Hollywood tells us it’s romantic to be persistent, that doesn’t make it a fact. If she hasn’t taken you up on any of your first three offers, she’s not going to on the 20th either.

Rather than frustrate both yourself and her, put the ball in her court and leave it be. If she’s bailed at the last second on three consecutive dates then you might want to go with something like this:

“Looks like you’ve got a lot going on at the moment. I have a bit of time free next week, if you’re keen to meet up just let me know”.

Simple, respectful and low pressure. Now if she really is interested and has had genuine reasons to keep cancelling, you’ll hear from her. If she was just too nice to say no, that’ll be the end of it.

Whatever the outcome here, consider it a good one. Either you’re finally going to meet or you’ve just stopped tipping your valuable time into a one-way affair.


There we go, the most cheesy ways to ask a girl out. Like so much of my outlook and advice on dating, it really comes down to respect for both you and her.

Dating is meant to be fun, not a strategic game of chess. Be upfront with her, strive to project confidence and enjoy the experience for what it is. No need for cheesy or cringe-worthy approaches!

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