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How to Ask a Woman Out on a Date with a Bulletproof Plan

How to Ask a Woman Out on a Date with a Bulletproof Plan

Dating is a rather modern dating trend.

Sure humans have been courting each other for millennia, but dating really only took root last century.

Dating back then was easier, simpler, and often involved a chaperone in the form of a relative breathing down your neck. Today, dating isn’t as simple as asking getting set up by your parents or asking the girl you’ve shared a pew with since the 4th grade if she wants to grab some ice cream.



Today, a first date often involves grabbing a drink with a complete stranger -not a woman that you’ve known since elementary school and that has lived in your neighborhood her entire life.

But just because how asking a woman out has changed, doesn’t mean you need worry about the process. In this concise article, we’ll equip you with the steps you need to take in order to ask a woman out on a date.

How To Ask a Woman Out on a Date

Harnessing The Power Of The TDL

There are two ways to ask a woman out. One involves asking her out on an amorphous date in the undefined future. The line, “Want to go out sometime?” fits snugly into this category. The other, more adroit, method asking her out on a specified date that demands a yes or no answer. This is what we call a TDL.

TDL stands for time, date, location.

When requesting a date, you’ll need to include the aforementioned information. This concrete date pitch gives her a tangible date idea to either accept or deny. An example of a TDL looks like this, “Hey Steph, considering we’re both huge Jazz fans, why don’t we grab a couple of drinks at the Bird Park on 5th avenue this Thursday at 8. Can you jive with that?”

Boom. TDL.

Juxtapose this with “Want to go out sometime?” Re-read the question. You’re not asking her out on a date. You’re asking her if she’d like to go out with you in the undefined future. A date idea won’t appear out of the blue and present itself, you’ve got to take control of the situation and ask her out on a specified date if you’re serious about dating her.

Leverage Social Media

how to ask a woman out on a date by social media

This tactic only applies to men that have been silenced on dating apps. Let’s set the scene.

You’ve matched with a woman and have chatted it up quite a bit to the point that you’re almost ready to ask her out with a TDL. There’s just once problem. Your most recent messages have been received with radio silence. You can capitulate and continue swiping or try for one last-ditch effort.

Find her on IG or FB and re-introduce yourself. Tell her that you weren’t able to connect with her on the dating app so you thought it best to carry on your correspondence via SM. After getting reacquainted, make your TDL pitch. Perhaps lead into the date pitch by asking if she’s into a certain type of food before asking her out to a restaurant.



Become The Hype Man For Your Own Date

asking a woman out on a date

Listen, not many people are willing to ditch the friends or break their routine to go out with a stranger. You need to make it worth her while. Do this by framing the date in such a way that she can’t possibly afford to miss out.

Don’t just invite her to Starbucks for a coffee. Instead, ask her to explore this new coffee shop that just opened up that’s brewing coffee from remote parts of the world. Effectively convey what makes your date unique.

Example: (Name of locations) serves the world’s best donuts (as an example) and they’re city-famous because (find a fun fact about why on the date location’s website). Want to go this Thursday at 7?

Example: Have you ever tried Veuve Cliquot sorbet? _____ (name of location) is serving it Saturday at 2pm, want to join me for a taste test?

Be enthusiastic about the date-to-be. If the sorbet doesn’t convince her to join you, your hype surely will.

Articulate Value

ask women out for a date

Dates -especially first dates- must be viewed as of value. Again, no one wants to grab a coffee at Starbucks with you or wine and dine at your local Chili’s. You’ve got one or two sentences to make this date seem badass -so how do you do it?

First, let’s understand the context. Asking a woman out to a concert or a Broadway play is inherently awesome. Few could muck up a TDL when it’s inherently kick-ass. The issue is that not all first or second dates will be inherently awesome places.

According to my MegaDating blueprint, a first date should last no longer than an hour and no more than $10 should be spent. So how do you make this date sound awesome?

As mentioned above, most likely this date location has a website that’s promoting their products or services. Use the company’s language, hell, plagiarize it if you have to, to make this first date sound appealing.

Make her understand what’s so great about this date. Send or a photo, paint a picture, wax poetic about the park’s new sculptures or the cafe’s new cold brew.



What If You’re Going Out Of Town Or Need To Delay?

There’s a certain tempo that online daters should flirt to.

Online conversations have a way of fizzling out if you wait too long in asking her out. After a few messages have been exchanged, you really need to ask for her number or ask her on a date.

There shouldn’t be more than a few days between the date pitch and the actual date. If you’re unsure of when you can ask her out, start hinting at the TDL by asking her if she’s been to a certain location or likes to do a specific activity. Learn more about her likes and dislikes so that you can craft the perfect first date. This is called planting the seed.

Once your schedule is free enough, ask her out on a date that’s three days away. If you know you can’t see her for a week or two, instead of making chit chat until you’re three days out, ask her if she’s available next Saturday. Then wait a few days to finalize the TDL.

But Isn’t A TDL A Bit Direct/Aggressive?

Half of Tinder users have never met up with a match. That means 50% of Tinder users are window-shoppers.

Either she’s also a window shopper, or she’s tired of wasting her time with men that don’t have the cajones to ever meet up.

Being direct for a change will be refreshing. If she feels as though things are moving to quickly she’ll tell you. Should this happen, exchange some witty banter for a bit before asking her out again.

Ask Questions That Lead Towards A TDL

The best TDLs involve activities or locations that she enjoys. To find out what she’s into, ask her. Learn about her hobbies, what her ideal Sunday afternoon looks like, if she’s into hiking, etc. Hunt down details about her that you can use to craft a dope TDL.

Other sample questions you can use to help construct a TDL are:

  •  Any fun plans for the holiday weekend?

  • Do you work 9-5? (Now you’re gaining insights about her schedule and availability)

  • What part of the city do you work in? (Here you’re gaining insight into where you can seamlessly plan a daytime date near her work)

  • Do you have a long lunch break? (This can help you determine whether to pitch a coffee date on her lunch break)

Create A Plan A, B, And C

So if we reverse engineer this, first you’ve got your location.



Hollow Coffee.

Now, what day and time make sense for this location? Remember Sundays and Mondays are bad days for first dates.

So Plan A is Tuesday at Hollow.

What time makes sense to meet with her Tuesday at Hollow Coffee?

5:30 pm or 6 pm.

Do you know if they’re open at that time? Check their hours on the website. Turns out Hollow closes at 3:30 pm. So now we have to think about what other day would make sense based on Hollow’s schedule.

They’re also closed on Tuesday and Wednesday so it’s a good thing to check that logistical stuff in advance of your date pitch. Then you’re going to make a fallback plan B and C, in case she’s not available on that day/time or can’t do the location for some reason.

My Signature Clients use a workbook with a tab full of date ideas that they create and in that tab, there are all kinds of notes that are made about what days and times are the best to go to different date locations so they don’t have to do all the work every time they pitch a date idea to a woman, it’s all right there in their spreadsheet for them (once they create their date plans).

Plan A Is Your First Choice Date Idea

Many men bemoan having to ask women out on dates. But doing so puts you in the driver’s seat. There are so many variables you can control by crafting the date idea. Here are some of the points you should consider when generating a TDL.

What is your ideal day to meet her for a date?

Example: Wednesday.

Now think about what time is most desirable to meet up with her on Wednesday.



Example: 6 pm.

Problem: It may be dark outside.

Can you instead do a coffee date on a lunch break? This might be difficult depending on where she works but that then becomes one of the questions that you ask.

Offer A Specific Time, Not A Time Range

Now, think to yourself; if I could do a daytime date on Wednesday, what time would that be?

Example: Anytime between 11:30 am and 1 pm.

Here you’re going to determine one specific time and if she can’t do it, then you can pitch a different time.

Example: Let’s do Hollow Coffee on Friday at 11:30 am.

She says “I can’t take lunch that early.” You overcome the objection with “no problem, how about 12:30 pm?”

Make things easy for her while keeping yourself in the driver’s seat by only proposing specified times, never a time range. She just wants to be able to say “yes” or “no.”

Go with Plan A, Then Wait for the Objection

If she objects, move to Plan B. Plan B, same location, different day. In case she can’t do the first day you suggest. Plan B could also be the same day and location, at a different time, if she objects to the time.

The most important aspect of a TDL is the location/activity. Once this has been decided upon it’s just a matter of figuring out what time and day works for the two of you.

Plan C: This Should Be Your Least Desirable TDL

It’s used as a fallback option if Plan A and B aren’t possible.

Example: Wednesday at 6 pm date.



This isn’t because first dates should take place during the day and not at a time when people naturally want to be eating dinner. If you’re using a new location for your plan B, make sure you have a clear value add that’s easy to articulate.

Imagine the value add is that a certain speakeasy has the most delicious mixed drinks with bourbon. What question do you need to ask her to determine whether or not to pitch this location?

Example: Do you like bourbon? OR Are you a bourbon drinker?

Need Help Planning Epic Dates? Book A New Client Session To Learn More About How I Can Help With My Signature Program.

Any screen talk prior to a date should move in such a way that it builds towards a TDL. If she doesn’t accept your date pitch the relationship ends before it can ever really starts. This time period is so fragile because effectively what you’re doing is trying to convince a stranger that you’re worth meeting IRL.

To become an expert at quickly building trust and pitching a high-quality TDL, consult with yours truly. Book a new client 1-on-1 Skype session with me today to begin your journey towards dating mastery. In our 3-month Signature Program, you’ll learn all the techniques necessary to master dating in 2020.

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