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How To Ask For A Second Date

By Emyli LovzSeptember 18, 2019Conversation
How To Ask For A Second Date

Wondering how to ask for a second date? Or when to ask for a second date?

Let’s start with the first date, which I’ll assume went well.

You two clicked, had some giggles and a connection was born. Now you want to keep the good times rolling with a second experience with her. Asking a woman to see you again after an awesome first date shouldn’t be difficult. If you two bonded well enough on the initial date, mumbling a bunch of intelligible noises followed by pronouncing a word that resembles date with an inquisitive inflection should score you a second date. However this is a classic example of how not to ask a woman out on a second date.


If you want to suavely ask a woman out, you’ll need to perform better than that. Here are a few things to keep in mind the next time you’re internally debating how to ask for a second date.

How To Ask For A Second Date

Women should always be asked out with a TDL. It doesn’t matter if it’s the first, second, or 34th date. TDL stands for time, date, location. Too often we see men ask women on amorphous dates. They’ll say something like, “hey, wanna get together sometime?” This is a half-ass way to ask a woman out. There is no date set, no activity proposed, no nothing. It gives her little to latch onto. When asking her out, make the request as concrete as possible. Such a request looks something like this:

Hey Ashley. Want to go on a graffiti tour with me this Saturday at 1pm?

You need to give her a clear event to say yes or no to. It’s all too easy for a woman to accept an invitation to go on a non-specific date in the undefined future. She’ll accept just to avoid any awkward situations from arising.

Women are Naturally Attracted to Confidence

It doesn’t matter what genitalia you’re working with, confidence is always attractive no matter your sexual preference. That’s the reason why asking her for a second date with a TDL is such a great idea. It shows her that you know what you want and that you’re not afraid to get rejected in person. A direct man gets what he wants. A scared boy will coward behind a phone as he flirts with a woman for days before asking her out.

It’s also important that you create a TDL interests her. If you’re following the MegaDating blueprint, you spent a mere one-hour with her on your first date. Think back to this date. Comb through your memory to remember her interests. Is she into hiking, painting, biking, etc.? Second dates should be kept active. Keep that money in your pocket and have the date revolve around an activity that gets you two moving. If you didn’t listen to what she was interested in, find her FB, IG, or dating profile to inform what you do on your second date.

Going further, try to create a date idea that you two are mutually interested in. If she’s a fervent bird watcher and you’re simply not, keep the binoculars at home and choose a different activity. You’re in control of the date’s location, time, and activity. Why would you pick an activity that you dread?

Make sure the second date is free, goes down during the daytime, is active, occurs outside, and encourages physical touching. If you’re at a loss on how to craft an awesome second date, I’ve got some ideas for you.


After You Pitched Your TDL

At this point the date has been set. Sunday at 2 p.m. you’re to meet at the new Rodin exhibit and make fun of this overly vaunted sculptor. You probably can’t wait. The issue is that you’ve got to wait three more days until you can see her again.

You now have her number and can text her at anytime. But refrain. It’s all too easy to start a meandering conversation via text. This is a surefire way to put out a spark. The date is scheduled so far away in order to build anticipation. Speaking everyday about the minutia of life will dull her opinion of you. There’s only so much gratification either one of you can receive from a digital conversation.

Only text her a day prior to the date. Check in with her and remind her that you’re stoked to go to the Rodin exhibit on Sunday. Don’t ask her about her week or what Netflix series she’s currently binging. Save the chit chat for the date.

For more tips on texting after a date, here’s an article that may interest you: What To Text Her After the First Date Including Examples.

When To Ask For A Second Date? 

I get this question every week from one of my clients. “Emyli, should I ask for a second date after the first date, on the first date, over the phone, via text?” 

Assuming that she’s still sizzling from the first date, you don’t want to wait long to ask her on a second one. Use that momentum to your advantage before it fizzles out. Here’s a few options, listed from best to worst:

#1 Best Option for Asking Her for a Second Date

Ideally you have a TDL in your back pocket before the first date even begins. This way you’ll be able to ask her on a kick-ass second date by the time the first date ends. Don’t play games by refraining from messaging her after the first date. Play that TDL card as soon as possible.

Even if the first date went well there’s always a chance that with time, things could change. Her feelings could wane after analyzing the date, another man could come into her life, or she could become distracted by work, friends, or other engagements. Don’t delay your request to see her again.

As the first date is coming to a close, use your pre-determined TDL to ask her on a second date. Don’t forget to specify the time, date, and location. If you later learn that the date won’t work out for whatever reason, amend it so that it does. The important part is that you’ve already asked and have received an affirmative to see you again.


#2 Best Option for Asking Her on a Second Date: The Phone 

This is your backup plan. Should a TDL not come to you, the moment not feel right, or you simply forget to ask her out at the end of the first date, you’ll just have to call her at a later time.

Don’t text her, slide in her DMs, or hit her up on Facebook. Calling is the way to go. That being said, there are some younger women that might feel uncomfortable talking over the phone. No worries. That discomfort will work towards your advantage. Calling someone is clearly more meaningful than a text. Even if it makes her feel weird for a second, ultimately she’ll be flattered that you decided to call her.

Most likely she won’t pick up. She’ll be busy, in a meeting, or have her phone away from her. When this happens leave a message. Simply say: “Hi Amber, this is Jeremy. Give me a call back when you’re free.” Chances are few if any guys have behaved this way before. Your short voicemail will leave her puzzled and intrigued. Once she calls you back, ask her for the second date.

Leaving a TDL on her voicemail gives her too much time to debate whether or not to go out with you. Instead, ask her in real time.

If she texts back, go with the flow. Shoot her a text asking if she’s down to take a jaunt through the MOMA at 2 p.m. this Saturday. Even if she responds to your voicemail via text she’ll still respect that you called rather than typing out a swift text.

Wondering when exactly to call her?

Call her three days before the proposed date. This is the sweet spot. Three days is enough time to let the anticipation adequately build. Too long and that anticipation will spoil. And if you try asking her for a second date a day after calling and she’ll be taken off guard and may have to decline due to other arrangements.

Don’t Force It

Not every first date works out. Some just fall flat. Realize when there’s no connection. This will save you both time, money, and mental willpower. This is why first dates should last no longer than an hour. It’s just the right amount of time needed to spend with someone to determine if there’s a connection. Spending one measly hour on a first date isn’t the type of investment in a person that compels you to need to see them again.


Think of the big picture. We all know how hard it is to break up with someone you’ve been seeing for months or years. Part of the reason we can’t let them go is because of all the time we’ve invested in them.

This simply isn’t the case when you follow the MegaDating blueprint for first dates. A first date should last no more than one hour and no more than a grand total of $10 should be spent.

Remember, Second Dates Build off the First Date

The ‘how’ in how to ask for a second date also relates to the first date. There’s no point in asking her out again if the first date went poorly. So how do you have an awesome first date?

Keep things light. MegaDating first dates only last an hour. Don’t get into deep or controversial topics just yet. There’s also no need to talk about how many children you do or want to have or who you voted for last election (unless the answers are dealbreakers).

Ask her probing first date questions that won’t dampen the mood. Show a genuine interest in her while keeping things light. Laugh, make physical contact, smile, listen, and be present. Also don’t forget to brush your teeth, read the news prior to the date, and enter the date in a good mood. If you do the aforementioned things it’s likely that she’ll agree to a second date.

Take The Lead

It’s true. Women today have more equality than ever. They can own land, work any job they want, attend college, win four World Cups, etc. Despite this newfound equality, there are still some dating traditions still around from the old days. Women have yet to be as proactive as men are when it comes to asking them out.

Don’t think that just because you asked her on the first date it’s up to her to initiate the second one. Societal norms still put the responsibility on the shoulders of the man in the relationship. If you wait for her to muster the courage to tear down gender norms, you’ll be waiting until your next period comes. It just won’t happen. The good news is that if you asked her out once, you can surely do it again.

The biggest takeaway from this article is that to secure a second date you must use a TDL at the end of the first one. Doing so is a strong indicator of confidence and interest.

I know this topic and dating in general can be quite puzzling. But there are people like myself who are here to help you. If you need support, go ahead and book a 1-on-1 New Client Skype Session with me. During this intro session, we’ll diagnose your dating issues, create an action plan, and see if my 3 month coaching program could help you reach your goals.