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Date Planning Guide: Second Date Questions to Ask a Woman

By Emyli LovzJune 25, 2019Strategy
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 with the woman you’re dating. By building on the conversations you had during the first date, you can strengthen your bond and escalate sexual tension. In this article, I’m going to provide you with several strategic second date questions to ask on your dates. The questions are designed to help you determine whether this is a woman you want to continue to pursue.

Keep in mind that you are still in the very, VERY early stages of getting to know each other. If your date appears uncomfortable with the sexier questions, shift back to lighter topics. 


I cherrypicked some of these questions from the now famous study, “The Experimental Generation of Interpersonal Closeness.” The article was published in the Personality and Social Psychology Bulletin. It was also featured in one of The New York Times’ Modern Love Essays. Here are my top 20 questions to ask on a second date.

Second Date Question #1: Favorite Family Member?

This question offers an excellent opportunity to get a little deeper without overdoing it. It’s likely that on the first date, you got to learn a bit about the woman’s family. Perhaps she’s told you how many siblings she has, if her parents live in town, whether they’re happily married, etc.

If she balks at the question or seems uncomfortable, don’t push it. A lot of people are not close to their families. Others may have bad experiences that make 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’s Kept You Here?

You likely already covered the “Are you from here?” question during the first date. This follow-up question is an excellent way to learn more about what made your date decide to relocate to her current residence or why she chose to stay put.

Question #3: 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. There are things about you that this lady enjoyed on the first date. Hence why she agreed to a second date. Why not push the envelope and encourage a little sexual tension? In return, tell her what you find captivating about her but avoid obvious compliments. 

Question #4: 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 question 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 #5: 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 question offers an opportunity for you both to become humanized to each other and even have a laugh.


Question #6: What’s Something You’re Terrible At Doing?

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

Question #7: 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 #8: Ask Her to Give You Two Truths and a Lie, and Try to Guess the Lie. Then Do the Same and Have Her Guess.

Here we have one of my favorite second date questions to ask. It reminds me of when my boyfriend and I first started dating. He would always ask playful questions on our dates that made conversation so much more fun.

Question #9: If You Could Give Your Middle School Self One Piece of Advice, What Would it Be?

Love this question because middle school was an awkward time for approximately 100% of us. A great question that can help each of you laugh and ease the tension.

Question #10: How Long Do You Usually Wait Before Kissing Someone?

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

Question #11: What’s the Worst Kiss You’ve Ever Had? What Made it Terrible?

This question is a way of easing into stoking the sexual tension. You guys can share a laugh over dating horror stories. Additionally, you can glean insight into how she likes to kiss. 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 #12: 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 #13:  What Are Your Rules for Good Sex?

As with #17, gauge her comfort level here, and if things go well, lead into question #14.

Question #14: What is the Craziest Place You’ve Had Sex?

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


Question #15: What Clothing Makes You Feel Sexy?

This question offers a fun way to activate her creative imagination. The second date is all about escalating sexual tension, so if you can get her mind thinking about sex-related things, you’ll be that much closer to converting your second date to a third.

Question #16: What Color Underwear Makes You Feel The Sexiest?

This question was one that somebody I date during my 100-date experiment asked me. It wasn’t something I’d thought about before, which made it all the more fun when it came time for me to answer. Thinking about what makes a woman feel sexy, makes a woman feel sexy. Isn’t that funny. Try it out yourself on a second date or even as a fun text before the third date. I also recommend you tell her that you want to see her in them. Does it push her buttons? Yes, but the risk is worth the reward.

Question #17: What’s Your Favorite Memory From Childhood?

I’ve had a lot of clients tell me this has been a good question for them. It’s useful because it brings up positive, nostalgic memories. Research shows that nostalgia can boost a woman’s mood and decrease stress. A question like this one can also provide deep insights into her family life, which is a highly charged, emotional topic. You’re always on the right track if your conversation leads to emotional responses. Avoid questions that only lead to logical answers.

Question #18: What’s One Thing You’ve Always Wanted To Do But Have Been Too Afraid To Try?

This is a great question and one that reveals ideas for where to suggest another date. If the woman you’re on a date with mentions always wanted to try salsa, you can use salsa as a compelling third date invitation. You already know she’s interested in the idea because she’s the one who thought it up. Now all you have to do is pick a date and time and you’ve got yourself a third date. Additionally, if she’s been scared to try it previously, you can be the guy that helps her overcome that fear. Doing so will demonstrate that you can keep her safe and lead her in the direction she’s always wanted to go. Now that’s MF sexy.

Question #19: What’s Your Favorite Part Of A Man’s Body?

This question is a fun way to get her thinking sexually. Everyone’s responses are different too, so this question is fun for two reasons: it stimulates sexual tension and provides deeper insights into why she might like you.

Question #20: If You Were On Death Row, What Would Your Last Meal Be?

This question is a subtle way of figuring out what her favorite food is. With this information, you can close for a third date at a restaurant that she’s guaranteed to like. What an effective way to get her to say “yes.”

Get More Dates with The Types of Women You Want To Date

The above second date questions will 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 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 new client 1-on-1 Skype session with me today. In our intro session, we’ll diagnose your dating history, uncover any specific issues you may be experiencing, create an action plan, and see if my 3-month coaching program could be a fit for you.