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

By Emyli LovzJuly 3, 2019Strategy
third date questions to ask a woman

Are you looking for third date questions to ask a woman? Well, then you’re in luck. First of all, if you’ve made it to the third date, then congratulations! To get to this point, you’ve undoubtedly won her trust, built rapport, and–fingers-crossed–established sexual tension. Kudos to you, my friend. 

When executed effectively, a third date can serve as a doorway, or bridge, into a more stable segment of the courting phase. The third date is also a time when couples frequently seal the deal. For this reason, third date questions should get a lot deeper. As such, the third date is a good time to gauge your moral and intellectual compatibility, as well as your sexual compatibility.

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). Asking emotionally compelling questions can also help to bring the two of you closer together. I cherrypicked some of these questions from the now famous study, “The Experimental Generation of Interpersonal Closeness.” The study was published in the Personality and Social Psychology Bulletin and was featured in the New York Times’ article Modern Love Essays. So, without further ado, here are my top questions to ask a woman on a third date.


Third Date Questions #1: Are You Religious?

Talking about religion isn’t taboo. Don’t be afraid to discuss this subject on a third date. Sharing similar spiritual beliefs is essential for a relationship to be sustainable. At this point, you’ve likely built a strong enough connection that you can enter into the spiritual, religious, and political territory.

The most important thing, when talking about religion, politics, and other controversial topics is to respond without judgment and to keep an open mind. If your date has vastly different religious views than you, get curious rather than judgemental. Ask questions that reveal the why behind her beliefs. Was she raised in a particular faith, or did she choose the spiritual practices that she now follows? 

Question #2: Did You Vote For Trump?

Politics can be incredibly polarizing, and that’s not a bad thing. Don’t be alarmed by a woman’s emotional reactions. Inciting a negative or angry response is a million times better than being forgettable. Chemistry is about emotion and sensation, not logic. If you can’t provoke emotional reactions in the women you’re dating, then you’re bound to wind up in the friend zone or worse. Plus, if you have incredibly different political leanings, it’s probably not going to work out romantically anyway, so why delay the inevitable? 

Some people consider interpolitical dating entirely off limits, but I disagree. Plenty of successful relationships, and even marriages, between Republicans and Democrats, exist. I mean, my boyfriend voted for Trump, and I’m a Democrat. The boy is crazy, but I still love him. 

Of course, if the girl you’re on a date with posits views that are red button issues for you, the most important thing to remember is to keep your cool. You can have a disagreement and still be respectful — in fact, disagreeing is healthy and sexy. No girl wants a yes-man. You have to have your own opinions and beliefs. To help you prepare for a potential (healthy) debate, and learn how to take a stand without offending her, read the problem with being too agreeable.

Question #3: What’s Your Favorite Part of a Man’s Body?

This question pushes the sexual envelope, and dammit if it shouldn’t be pushed on a third date. The sexual tension you established on the second date needs to be elevated on the third. After all, you’re not only looking for a best friend here. You’re looking for a lover, a confidant, a companion, and a playmate. In other words, you’re looking for the total package–aren’t you?

Sexy conversations should be a part of date number three. Pushing the boundaries is a good thing, especially when it comes to verbal communication. Play it too safe, and the woman you’re dating will plop you right down in the middle of the friend zone. Whereas, discussing sex with confidence, demonstrates to a woman that you’re confident and secure enough to figure out where she stands with you.

Flirty dialogue creates a safe space for you to gauge her interest level without violating any personal, physical boundaries. While it may feel risky to ask leading questions, it’s a helluva lot better than hanging out in limbo while she falls for some other guy. Plus, everyone knows that a confident man is an attractive man.


Question #4: What’s Your Opinion On Stay-At-Home-Dads? Are They Real Men?

Like the political subject, this question offers a more in-depth insight into her value system. Examine how her views align with yours. 

Question #5: Who’s In Your Top Five?

Many couples have a “freebie list” that consists of five celebrities they’d be allowed to hook up with if the opportunity presented itself. I like this question because it’s goofy, and shows that you’re secure with yourself. Asking this question will prove that you’re not the type of guy to puff out his chest and start seeing red when she sees a Ryan Gosling poster.

Question #6:  What Are You Most Afraid Of?

This question offers up an opportunity for both of you to demonstrate a little vulnerability without getting too sensitive. Sharing emotionally exposing stories with one another creates deep sentimental connections, unlike the bonds you share with friends or coworkers. And, a rich, soulful connection can be the differentiator between how a woman feels about you and how she thinks about the other guys she’s dating.  

Question #7: What Do You Spend The Majority Of Your Time Doing?

As I mentioned, the third date is often a make-it-or-break-it affair. After the third date, you might realize that you don’t want to continue the relationship. On the other hand, this date could seal the deal for both of you.

Asking the woman you’re dating what she spends the majority of her time doing, speaks volumes about what she values most in life. It’s easy to say that family comes first, but if she’s spending 10 hours a day working, then family isn’t her main priority right now. Are you cool with that? Learning what’s most important to her — and vice versa — is essential, because having similar values is part of what makes for a healthy and sustainable relationship.

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

The locations people spend their time can tell you a lot about their personality. If she likes to chill at home, go to the beach, and hit a friendly jazz club, you can probably guess that she’s pretty laid back. Alternatively, if she likes to spend her time rock climbing, traveling and skydiving, then you’ve likely got an adrenaline junky on your hands. You devil you. 

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. For instance, if you get energy from socializing with friends, but going out all the time zaps hers, the writing might be on the wall. You can’t force compatibility.

Everyone is on their best behavior when they first meet. But, the truth eventually comes out, so why not lead with it from the start. Showing up as the authentic man that you are, right from date 1, will help you sidestep major blowups and social collisions. It will also help you to find the woman you’re genuinely searching for much faster.

Third Date Questions #9: What’s Your Guiltiest Pleasure?

This question offers a fun and flirty opportunity to exchange juicy stories, and it might even get her in the mood. During moments of laughter, when you ask these sorts of questions, be sure to practice some touching. The power of touch is beyond verbal reasoning, it speaks volumes. Don’t be afraid to communicate interest by touching the small of her back, brushing the hair off her should, or leaning in for a kiss when the mood feels right. Trust me, you’ll be glad that you did. 


Question #10: What Are You Most Grateful For?

This question is a great way to deepen the conversation and get to know her better. Gratitude demonstrates humility. And, if she’s not grateful, she’s probably an a-hole, so maybe it’s better if you bounce. Just sayin’.

Question #11: Have You Tried…?

This final question can be strategically woven into conversation in a way that plants a seed in her mind. Your end-goal here is to have sex and to do that; you’ll first need to convince her to come back to your place. To do this effectively, you’ll need to give her a reason that isn’t explicitly sex-related. The line, “hey baby, wanna come back to my place and shag” isn’t likely to win you the golden ticket. 

Why? Because women have natural defense mechanisms in place to shut down sex. You can avoid this by having a seemingly unrelated reason for her to come back to your home. For instance, knowing how to make a tasty signature drink can be one of a few compelling reasons for a woman to go back to your place.

There are several easy drink recipes out there too, some that use as few as three ingredients. I’d give the drink a distinctive name so that it sounds more like a once in a lifetime opportunity for her to come to your place and try it. Rather than asking if she’s had a dirty martini–which everyone has had–why not say, have you ever tried a White Russian Gummy Bear Martini? Sounds a lot more exciting and mysterious. Let her curiosity be the reason she says yes to your invitation. 

Other examples include the following: If you have a dog she’s never met, ask her if she’d like to meet Mr. Pickles. Or perhaps you have an amazingly delicious exotic rum (Zaya is yummy) that she has to try. Alternatively, you could tell her you’ve just come back from a wine tasting event and have the most delicious champagne back at your place that she has to try. You could also ask her if she’s ever tasted Hangar One Mandarin vodka. It’s as fragrant as perfume and is handmade in an old airplane hangar, hence the name. You get the picture, the ideas are endless.

A Quick Note About Consent

Just because the third date is often the time when couples first have sex, it 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 have sex, great. If she doesn’t, that’s fine too. A crucial thing to keep in mind is consent. No, always means no.

Having sex for the first time with someone can be a big deal for a woman. If there’s any history of sexual trauma, sex might trigger post-traumatic stress disorder. Other times, a woman’s religious or spiritual beliefs might strongly oppose sex before marriage. Or, if she’s just been a regular, living, breathing human girl raised in America’s stuffy Puritan culture, then social pressures could be responsible for her prudent nature.

Regardless of the cause, sex in America, especially in our modern reality, comes with a lot of social pressure. And believe me, I 100% understand that it happens for men too. The Me-Too movement is fantastic for women, but it also creates a ton of confusion for men around sex. Navigating masculinity, femininity, and sexuality today is complicated AF.


Things could go amazing on your third date, 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 types of consent, check out this video from Blue Seat Studios.

Ace Every Third Date

Having a good list of third date conversation starters is just the beginning. You also need to have stellar answers to those. A woman is more often than not, going to respond with, “Oh, I don’t know, that’s a tough one. How about you?” And when she does, you’d better be ready with a killer answer that demonstrates some wicked sexy morals and values.

Want to make sure to ace your upcoming third date? How about ace-ing all of your dating and relationship goals? If so, I’m here to help. My clients and I train in-depth on conversation and storytelling in my Signature Program. And, once clients master these advanced topics, no date or social interaction is ever the same.

The teachings in my Signature Program are all evidenced-based and originate from my 100-date experiment. During that time, I gained a wealth of knowledge on the intricacies of the modern dating world. Now I know what works and what doesn’t in dating, and I help men understand how women think so they can find their ideal partner, just like I did.

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