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How to Ask a Woman Out on a Dating App, Correctly!

How to Ask a Woman Out on a Dating App, Correctly!

Today’s topic is on how to ask a woman out on a dating app. As a personal dating coach, I get asked for tips on how to ask women out online all the time, and it’s one of my favorite topics.

While on my 100-date experiment, I became very familiar with the ins and outs of online dating and used some great dating sites (here’s a list of my favorite free dating sites and apps) to connect with people and fill up my social calendar. I received a lot of messages everyday from guys wanting to talk to me or ask me out and learned quite a bit about what kind of direct messages piqued my interest in someone and what turned me off.

If you’re wondering how to ask a girl out on a dating app, I have good news — and bad news. Feel free to keep reading below to learn more, or watch my YouTube video if you’re a visual learner.

The bad news is that online dating is just as competitive as dating offline.

Attractive, successful women with dating profiles are bombarded with messages from guys on a daily basis. Some women receive up to 100 messages per day or more, so if you’re writing to her without a strategy, your message is likely to be ignored.

Still, being ignored is far better than the in-your-face rejection that could happen when asking a girl out in person. Asking a girl out online is relatively easy compared to asking her out face-to-face, but a lot of guys still get stuck at this important step.

Now for the good news.

There are a few tried-and-true ways to put yourself way ahead of the pack. Take a look at these guidelines and tips on how to ask a woman out on a dating app, and increase your chances of scoring that date.

How to Ask Out a Woman on a Dating App, Correctly!

First Message: Personalize, Personalize, Personalize!

Even if you’re messaging many women a day, you’re going to want to personalize the heck out of your first message. The first message should be sweet, thoughtful, and polite all while expressing your interest in her personality — not her looks.

Read through her profile and find some common ground — a shared interest, hobby, educational background — anything. You can use this as a starting point to relate to her through your similarities, which could help to create a sense of familiarity and closeness.

For example, let’s say that you’re both avid baseball fans. You could mention your loyalty to the Giants, while lightly teasing her for her passion for the Oakland A’s — and tell her you’d love to hear her thoughts on why they A’s are so bad sometime.

Chatting Before a Date: 10 Messages or Less

If your first message gets a response, congratulations — she’s interested. You might think this is the time to ask about her hobbies, hope and dreams family, etc.

Spoiler — it’s not.

No one wants to message back and forth forever without making plans to meet. Don’t leave her wondering whether you’re serious or just wasting her time like so many other online users. 

When planning on how to ask a girl out on a dating app, keep in mind that she’s probably getting messages from other men, too — and perhaps from more straightforward types that won’t waste time. Take action and keep your messages to 10 or less before setting up a time and location to see her in person.

Every message you send should build towards asking her out.

Crack a joke or two, riff on a shared interest and then BAM, ask her out: using a TDL.

Be Direct – Setting a Time, Date, and Location

Some clients of mine have recently received some pretty poor advice.

They were told that the best way to ask women out is to first ask for their calendar.

Look, as a professional dating coach — and a woman — I can say with some authority that this way is 100% wrong.

Look you’re not trying to book an eye exam, you’re trying to date some hottie you met on Tinder.

Asking a woman for her schedule makes you look:

— Desperate

— Like a creep

— Lonely and like you have zero plans in your near future

— Low value

— Did I say creepy already?

Take the interaction by the reins and propose a kick-ass date at a time that works for you.

Look, women have approximately a billion romantic options at all time.

In order to convince a beautiful stranger that she should spend her Friday night with you, you’ll have to ask her out on an amazing (or at least an amazing-sounding date).

This is why you should use a TDL.

TDL stands for time, date, location.

When asking a woman out you should explicitly ask them on a date that takes place at a specific time, on a specified date, and a location.

Without this information, your date is too nebulous to be real.

Sans this info you’ll likely to just say, “Hey wanna go out sometime?” Even if she were to say yes, you still won’t have agreed to go on a concrete date.

Use a TDL to give her something real that she can either accept or reject.

Make Your TDL Kick-Ass

Just because you specify your date doesn’t mean she’ll be down to clown.

In order to score a date with a strange and beautiful woman you’ll need to make your date activity super compelling.

In an ideal situation, you’d be hitting a concert or going to an observatory to watch an eclipse.

But these opportunities aren’t always possible and even if they were you wouldn’t want to take all your first dates to time and money-consuming events like these.

With that said, how do you ask a woman out on a banal date while making it sound once in a lifetime?

Your goal here is to make even basic date plans sound awesome, compelling, and time-sensitive.

For example, coffee dates are super commonplace first dates. They’re quick, cheap, and easy — all good things.

Let’s see how we can turn, “hey wanna get coffee this Tuesday?” into a compelling TDL.

First, you’ll want to bait her interest.

Tell her something like, “Did you know Starbucks has a secret menu?”

You can add value to your date idea by showing her something new or epic.

If it’s not Starbucks you’re going to tell her about some new coffee joint that’s selling a special item only at a certain time. You might tell her, “I’m going to try out this *new special amazing thing* at 12 tomorrow, want to explore with me?”

Let’s see how this formula might work with something wholly unrelated to coffee.

Should she like hiking, ask her if she’s been to a super cool mountain or checked out this amazing hiking trail, or has watched a sunset from a specific peak. Tell her that for whatever reason it’ll be amazing to go this weekend (sky will be clear, weather will be amazing, etc.) and then ask her out all the while specifying the time, date, and location.

If you’re worried that she’ll hate the plans you choose, and want to get to know her a little better — try something I learned from one of the guys I dated during my 100-Date Experiment. I call it the “2-Option Close”.

Expect Her Objection and Overrule It 

Rejection is part of the game.

If you ask out enough women — regardless if you use a TDL or not — you’re bound to get rejected.

Make rejection a learning lesson rather than a reason to stop asking women out.

But before I go on a spiel about the power of rejection let’s first talk about how to overcome a rejection.

If she says she can’t do a certain day, try moving the date a couple of days sooner or after. Again, avoid asking her what her schedule looks like. This will make it seem as though you’ve got nothing going on.

News flash, women want men that are coveted and have unique, nuanced lives of their own, not guys that wait around for strangers they met online to be available.

If you’re asking her out on the app, you can always say, “Bummer, well let’s plan something for next week, you should give me your number so we can make plans.” This way you’re off the app and can call her when you ask her out.

Another objection she may have is that she’s not into the date idea. If that’s the case again, ask for her number and come back with a date idea that you know she’ll be into.

Get Off Messaging and Get Her Phone Number

When planning on how to ask a girl out on a dating app, make sure to include a request for her phone number — especially after setting a date with her. Once you’ve decided to meet offline, you won’t want to continue communicating with her through the dating app.

Some women will be hesitant to give out their personal number before meeting in person. Try to keep the pressure off of her by giving her a casual reason for needing it. For example, you will need a quick way to contact her in case you can’t find her at the cafe, or wherever you decided to meet each other.

Once she gives it to you, make that the primary means of communication.

Don’t message her on the dating app again!

Texting her will seem much more personal and will give real-life perspective to your potential relationship, vs. chatting on the dating site.

Refrain from messaging her prior to the date. A date before simply confirm that you two are still on. When doing so, don’t ask her, “hey are we still on for tomorrow?” This gives her the opportunity to back out.

Instead tell her, “Stoked to go bowling tomorrow. Be ready to get your butt kicked.”

Now It’s Time To Ask Her Out

Crack open that phone, get to talking, and use a compelling TDL to ask out the woman of your dreams — or the woman you just matched with, whichever comes first.

If you need a bit more guidance, you can talk with a real-life dating coach (cough cough, moi) via a 1-on-1 Zoom call.

I’ll walk you through the process and answer any questions you might have about dating in 2021, and of course we’ll discuss if ongoing coaching might be right for you.

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