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Date Planning Guide: Second Date Questions to Ask a Woman

By Emyli LovzMay 2, 2018Strategy
second date questions to ask a girl

You had a great first date and now you’ve made arrangements for a second date. Congrats! 

The second date is a great time to go a little deeper and learn more about her by building on the conversations you had during the first date. In this article, I’m going to provide you with several strategic second date questions that can help you see if this is a woman you want to continue to pursue, and potentially get to the third date.

Keep in mind that you are still in the very, VERY early stages of getting to know each other. If any of the following questions listed here seem to make her at all uncomfortable, shift back to a humorous, more surface-level question. Don’t return her anxiety with more anxiety, and remember to keep things light and fun.


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. Here’s my top 18 questions to ask on a second date:

Second Date Question #1: Which Members of Your Family Are You Closest To?

This is a great way to get a little deeper without going too deep. It’s likely that on the first date, you got to learn a little bit about the woman’s family — how many sisters or brothers she has, if her parents live in town and are still married, etc.

If she starts offering up information (for example, “I was a tomboy growing up, so my dad introduced me to a lot of things like…”), you can get a little deeper by learning about some treasured memories she has with close family members.

Remember that if she balks at the question or seems uncomfortable to not push it. A lot of people are not close to their families or may have been through things in the past that makes them not want to go into a reverie.

As mentioned in the introduction, give her a casual but compassionate, “No worries!” and move on to a different question or subject — preferably one that is lighthearted and can make her laugh.

Question #2: What Made You Decide to Move Here OR What Has Kept You Here?

You likely already covered the “Are you from here?” question during the first date. This is a good way to learn more about what made your date decide to relocate to your current residence or why they chose to stay put.

Question #3: What Was the Most Recent Relationship You Were In?

Obviously, you want to pose this question in a non-threatening sort of way. But this can also be a great way to take inventory of any potential red flags.

If the girl you’re on a second date with JUST got out of a relationship, there’s a chance she hasn’t had proper time to heal from the heartbreak and could be emotionally unavailable.

There’s also a chance that she is recently divorced, which can be tricky business. People who have recently gotten a divorce have gone through a separation process, which takes time. It’s possible that during this time they were able to heal and come to a place that they can healthfully date again, but that often isn’t the case. To help you navigate the right path on this tight-rope of a subject, check out my advice on dating a recently divorced woman.

Finally, if her answer to this question is, “I’m actually still IN a serious relationship” — RUN!

Question #4: What Was the Longest Relationship You Ever Had?

Be prepared that her longest relationship could have been a matter of years — or as little as a few months.


If she hasn’t been in a super long relationship, that doesn’t necessarily mean she’s emotionally available or unable to successfully have one. And if she tentatively admits that her relationship history is pretty sparse, make sure that you aren’t visibly aghast (“REALLY?!”). Say something like, “Totally. It can be hard to find the right person.”

By being empathetic and relaxed at the same time, you’ll put her mind at ease.

Question #5: What Are Your Feelings on Marriage and Kids?

It’s an interesting time to be participating in the dating scene. According to research, a historic number of Americans are single, and a projected 25% of American millennials will never get married.   

A caveat of this trend can be that — for those who have a goal to meet someone to settle down with and start a family with — you may tend to attract more and more people who are not looking for the same kind of commitment as you. But I feel like the positives definitely outweigh the negatives.

With progressive times comes more choices. There are less and less people who think settling for a mediocre relationship is something they need to relegate themselves to. And another positive is that asking the question, “What are your feeling on marriage and kids?” isn’t so taboo.

Asking this question is just one more way to deepen that initial connection you garnered on the first date and it also gives you some good information for the long-term.

Question #6: What Made You Decide to Go on a Second Date With Me?

Make sure you pose this question in a fun, casual and flirty way. Obviously, there are things about you that this lady enjoyed on the first date — so much so that she agreed to a second date — so why not hear about all the awesome things about yourself?

And in return, make sure you let her know what was captivating about her, that it made you want to spend more time with her.

Question #7: If a Crystal Ball Could Tell You the Truth About Yourself, Your Life, Your Future, or Anything Else, What Would You Want to Know?

This is another way to get to deepen your knowledge of someone — and possibly even find out something unexpected — without posing a question that seems threatening or too personal for a second date.

Question #8: Before Making a Phone Call, Do You Ever Rehearse What You’re Going to Say? Why?

Chances are you’ve done this at least once. This questions offers a chance for you both to become humanized to each other and even have a laugh.

Question #9: What’s Something You’re Terrible At?

In this scenario, it’s a good idea to volunteer to go first and charm her with some humorous self-deprecation.


Question #10: Would You Rather Fight a Horse-Sized Duck or 100 Duck-Sized Horses?

A question that — no matter how long it’s been around — incessantly begs to be asked.

Question #11: What Does Friendship Mean to You?

Committed romantic relationships are built on a foundation of friendship. Her answer to this question can help give you insight into whether or not certain values each of you have will align.

Question #12: Ask Her to Give You Two Truths and a Lie, and Try to Guess the Lie. Then Do the Same and Have Her Guess.

This is one of my favorite second date questions to ask her because it reminds me of when my boyfriend I are first started dating. He would always bring one or two game-like questions to the date that really made me enjoy myself!

Question #13: If You Could Give Your Middle School Self One Piece of Advice, What Would it Be?

Because middle school was an awkward time for approximately 100% of us, this is another question that can help each of you have a laugh and ease any tensions.

Question #14: How Long Do You Usually Like to Wait Before Kissing Someone?

If she and you already kissed on the first date, you don’t need to ask this question. 🙂

Question #15: What’s the Worst Kiss You’ve Ever Had? What Made it Terrible?

This is a way to kind of ease into stoking the sexual tension. You guys can share a laugh over dating horror stories, but you can also learn more about ways she likes to be kissed. Plus, just the fact that you’re talking about kissing is likely to make her think about it, and get her in the mood.

Question #16: In Your Opinion, What Makes a Person Sexy?

Depending on how comfortable she seems with this question and how comfortable you’re feeling at this point, you can ask question #17 after this.

Question #17:  What Are Your Rules for Good Sex?

As with #17, gauge her comfort level during this question and then you can lead to our last question, which is…

Question #18: What is the Craziest or Most Embarrassing Place You’ve Had Sex?

Proceed with this question if she has been relaxed and comfortable with the other questions that are meant to stimulate sexual attraction.

Get More Dates with Women You’re Really Into

The above second date questions will definitely help you progress to the third date and eventually help you get into a full on relationship. But what if you aren’t even getting to the second date?

If this is the case for you, I’m here to help. As a dating coach, I’ve helped tons of guys just like you discover the fun that can come from dating by using strategic tools, such as megadating.


Megadating is a strategy that involves dating several people at once in order to diffuse energy, increase confidence and keep you from settling for the mediocre. It worked for me and it can work for you too!

Head over to my calendar and book a 1-on-1 Skype session with me today. We’ll get you moving in the right direction, fast.