was successfully added to your cart.

Date Planning Guide: Third Date Questions to Ask a Woman When Searching for a Real Relationship

By Emyli LovzMay 3, 2018Strategy
third date questions to ask a woman

If you’ve made it to the third date, then congratulations! The third date often can solidify whether or not you and that special lady will want to soon make an exclusive commitment and it’s also the time that couples often seal the deal. For this reason, third date questions should get a lot deeper.

The third date is a good time to gauge your compatibility, based on things like morals, values, and intelligence.

To help you out, I created a list of questions that can strategically help you to decide whether or not you want to take things past the third date (and back to your place), and that will also help to bring you and her closer together.


I cherrypicked some of these questions from the now famous study, “The Experimental Generation of Interpersonal Closeness,” which was published in Personality and Social Psychology Bulletin, and was also featured in one of the The New York Times’ Modern Love Essays.

Without further ado, here’s my top questions to ask a woman on a third date:

Third Date Question #1: What Are Your Spiritual Beliefs?

At this point, you’ve likely built a strong enough connection that you can enter spiritual, religious and political territory. The most important thing to remember in these circumstances is to respond without judgment and to keep an open mind.

Question #2: How Do You Lean Politically?

Politics can be extremely polarizing, which is why I don’t recommend treading into political territory very much until the third date. As with spiritual beliefs, be sure to respond without judgment and an open mind.

Some people consider interpolitical dating completely off limits, but I disagree. Plenty of successful relationships — and even marriages — between Republicans and Democrats exist. Of course, if the girl you’re on a date with posits views that are huge red button issues for you or says some things you consider EXTREMELY off the wall (i.e., “I think it’s about time we start aligning with koala bears when it comes to national security and sell marijuana to cats!”), the most important thing to remember is this: keep your cool.

You can have a disagreement and still be respectful — in fact, disagreeing can actually be a healthy thing.

To help you prepare for a potential (healthy) debate, check out my article on the problem with being too agreeable, which will offer you insights into why women value opinions and how you can take a stand without offending the woman you’re with.

Question #3: What Irritates You About the Opposite Sex?

This question can also spark a healthy debate, but it also shows that you are confident and secure enough with yourself to hear something less than flattering about your fellow man without taking it personally.

And a secure man is an attractive man.

Question #4: What Are Your Views on Gender Roles?

Like the political subject, this question will offer you insights into her value system and you can see how it aligns with yours.

Question #5: Which Celebrity Is Number One On Your “Freebie List”?

The last few questions can be a bit intimidating, so let’s lighten it up, shall we?


Many couples have a “freebie list” that consists of five (or more if you feel like being GREEDY) celebrities that they would be allowed to hook up with if the opportunity presented itself, and said hookup wouldn’t be considered cheating.

I like this question just because it’s fun and silly, and it shows you’re secure with yourself, i.e., you’re not the type of guy to puff his chest out and see red when your girl swoons over a Ryan Gosling poster.

Question #6:  What Are You Most Afraid Of?

This is an opportunity for both of you to get a little vulnerable without getting too vulnerable.

Question #7: What Are Your Top 3 Values?

As I mentioned, the third date is often the make or break one — you could realize you don’t want to continue on to a relationship, or this could seal the deal for both of you.

Learning about what she values — and vice versa — is important, because having similar values is part of what makes for a healthy and successful relationship.

Question #8: Where Are the Top 3 Places You Spend Your Time?

Where people spend most of their time can tell you a lot about them. If she likes to chill out at home, go to the beach, and hit a nice jazz club, you can probably guess that she’s pretty laid back.

If she likes to spend her time rock climbing, traveling and skydiving, you’ve got an adrenaline seeker on your hands.

There’s nothing wrong with either type of personality, but understanding more about her can help you get a better idea of your long term compatibility.

Question #9: What’s Your Guiltiest Pleasure?

This is a fun and flirty type of question where you can exchange stories and can potentially even start to get her in the mood.

It’s important for me to note at this point that you should definitely be stoking the sexual spark between the two of you by touching her. During moments of laughter when you ask these sorts of questions, be sure to practice some touching on her knee, shoulder, elbow and other non-threatening areas. At this point in your dating stage, you’ve likely become close enough as well that you can clasp her hand across or under the table.

Question #10: What Are You Most Grateful for, Right Now, At This Very Moment?

Disclaimer: If she doesn’t exclaim, “YOU!” don’t get offended — a third date is a big deal, but it’s not exactly a my-sister-just-had-a-baby-and-now-I’m-an-aunt-for-the-first-time type of big deal.


This question is a great way to simply continue to deepen the conversation and get to know her even better.

Question #11: What, If Anything, Is Too Serious to Be Joked About? 

This is REALLY important to know, so that you don’t unintentionally offend her.

Question #12: Have You Tried This Rare Drink?

This final question can be weaved into your third date bounce back (as in, bounce back to your place) plan. Knowing how to make a tasty, little-known drink can be one of a few compelling reasons for a woman to come back to your place and potentially seal the deal.

There are several easy drink recipes out there, some that use as few as three ingredients.

A Quick Note About Consent

Just because the third date is often the time that couples close the deal sexuals, that certainly doesn’t mean that it has to happen or that you should be completely banking on it. 

If she consents to go back to your place and then having sex, great. If she doesn’t, that’s fine too. A crucial thing to keep in mind is consent.

Having sex for the first time with someone can be a big deal for someone, and come with a lot of pressure. Things could go amazingly, things could go just fine, or things could not GO at all. Regardless of the events leading up to intimacy, no still means no. And no can come in the form of verbal and non-verbal cues.

If you or anyone you know is having trouble understanding different forms of consent, check out this video from Blue Seat Studios.

Ace Every Third Date

Having a good list of third date questions is just the start. Want to make sure you ace your upcoming third date? How about ace-ing all of your dating and relationship goals?

If so, I’m here to help.

During my 100-date experiment, I gained a wealth of knowledge on the intricacies of the modern dating world. By the end of the experiment, I had also found a happy, long-term relationship and you can find one too.


Want to learn more? Book a 1-on-1 Skype session with me today. During our introductory session, we will discuss your dating roadblocks, create dating goals, and also an action plan to help you overcome those roadblocks and find the girl of your dreams.

I also invite you to check out my Dating Profile Services. Whether you need a professional dating profile writing service or would like someone to review and assess your current profiles, I’ve got you covered.

Finally, my comprehensive online dating course will teach you all you need to know to attract gorgeous women, find a high-value girlfriend and avoid the friend-zone.