Are you wondering what to talk about on a first date? First dates are nerve-wracking. You want to make a good impression and connect. However, there is a lot of awkwardness that comes with getting to know someone on a romantic level.

But it doesn’t have to be that way. If you enter the first date armed with the right questions, confidence and a dash of charm, you’ll be on your way to success.

Take a look below at a few first date conversation starters along with some of my expert dating tips!

What To Talk About on a First Date, Question #1: Do You Have Any Brothers or Sisters?

If you’re wondering what to talk about on a first date in relation to their background, touching on the family is a great place to start. Ask your date if they have any brothers or sisters. And if they do, you can follow up this question with something like:

• Did you connect more to your brother or sister more? Why?
• Do you like being an only child?

Question #2: What’s Your Best Childhood Memory?

This is also a great follow-up to my first question.

Question #3: If You Could Only Eat One Thing for the Rest of Your Life, What Would it Be?

This is a creative spin on the typical “What’s your favorite food?” question. Moreover, her answer can give you ideas for where to take her to dinner in the future.

Question #4: What’s One Hobby You’d Like to Pick Up if You Had the Time and Money?

This is a great question because it encourages more than a “yes” or “no” answer and provokes thought. Make sure to ask follow-up questions like:

• What made you come up with that answer?
• Do you have hobbies similar to that one?

Think about something you’d like to pick up one day as well and share it.

Question #5: What’s Something That Would Surprise Me About You?

When it comes to figuring out what to talk about on a first date, keep fun and flirtation in mind. This is an innocuous yet playful way of getting her to share a little secret part of herself with you. And if she has trouble thinking about anything, you can say something like, “If you tell me yours, I’ll tell you mine.”

Be sure to share something about yourself as well. Remember, this date is all about building rapport.

Question #6: Describe a Perfect Day for You

Depending on how doable their perfect day is (i.e., if it involves cliff diving in Rome followed by dinner in Paris, this won’t count as a realistic third date), you can try to recreate that — or at least elements of it — during future dates.

Question #7: What Do You Consider Your Best Trait?

Figuring out what to talk about on a first date isn’t all about keeping the conversation going. You can also use it as a way to weed out red flags.

If the person you’re with gets uncomfortable and can’t think of one nice thing to say about themselves, that’s a bad sign. They may have low self-esteem, which never bodes well for a relationship.

Conversely, if they keep waxing poetic about all the things that make them superior to other people, you could be dealing with a narcissist.

Question #8: What’s Your Biggest Pet Peeve?

Whether it’s snorting, people who make “mm” sounds when they eat, or tardiness, it’s important you learn about her pet peeves. Why? Well, once you know what they are, you can hopefully avoid unintentionally ticking her off.

Question #9: Where Are You Originally From?

Find out if she’s a transplant or has grown up in your city. Either way, this provides you with the opportunity for follow-up questions, like:

• Did you go to school here? What was your major?
• What made you decide to move?
• What’s kept you in this city/county?

Question #10: What is Your Favorite Alcoholic or Non-alcoholic Drink?

This is another one of my favorite questions to get to know someone on a first date because it’s not as generic as the “favorite food” question and it also can give you something to fuel plans during the third date (IF appropriate) to take her back to your place.

Question #11: What is Your Favorite Travel Destination?

And you can follow this one up with, “What is one place you would love to travel to that you haven’t visited yet?”

Question #12: If You Could Pick One Famous Person to Have Dinner with, Who Would it Be and Why?

This is always a fun question. Make sure you come ready with an answer of your own. And like some of the other questions I have listed here, this offers tons of opportunities for follow-up questions.

Question #13: How Would Your Friends Describe You?

Someone who has a network of friends and, more importantly, friends who speak highly of them is someone you want to be around. This is another question that allows you to learn more about your date while also spotting any potential red flags.

Question #14: What Was Your First Impression of Me?

Hopefully, she’ll give you a compliment! If not, um, RUDE. She might not be the best match.

This question provides you with an opportunity to tell her something you really liked about her when you first met, which can escalate the chemistry between you two. If you’re stuck on what to say, consider doing something like comparing her to a celebrity.

Women love to be compared to women they admire. Before the date, think about someone pretty and inspirational that she resembles. For example, Natalie Portman or Rachel McAdams would be great picks.

Lindsay Lohan? Er…not so much. (Sorry, Lindsay.)

Question #15: What Does a Standard Weekend Look Like to You?

Use this to find out if she’s:

• A morning person or a night owl
• An introvert or an extrovert
• How she and her friends typically operate when the work week is over and it’s time to let loose
• A heavy drinker
• Her favorite movies to go see or watch at home etc.

Now that you know what to talk about on a first date, let’s take a look at some first date tips. The following tips will help you enter this date with a healthy mindset and confidence.

First Date Pro Tip #1: Don’t Take Yourself Too Seriously

A lot of people find that they bury their chances of getting a second date by allowing themselves to be overcome with anxiety on the first date. You’re worried about making a good impression and suddenly authenticity goes out the window. You’re unable to act like yourself and, moreover, you fail to infuse the date with wit and charm — two things that are extremely important when it comes to building chemistry.

Don’t take yourself too seriously. Ask yourself, honestly, what is the worst thing that could happen on the date? Are you afraid you’ll spill something? Say something stupid? That she won’t be interested in you?

Even if all of those things happened, it’s not the end of the world. Anxiety alters our perception in a way that makes menial things seem borderline life-threatening.

I’m not telling you to stuff these thoughts and feelings away. But acknowledging your worries and looking at them objectively can help you gain more self-awareness. This will help you loosen up and not take yourself too seriously.

One thing you can also do is smile. Even if it’s a forced smile, the simple act of smiling has been shown to relieve stress and elicit a sense of well-being.

Tip #2: Prep in the Morning

Get ahead of your first date jitters by doing some early bird preparation. One of the best ways to prep yourself for a first date — or anything else that prompts anxiety — is taking a jog. Along with the various cardiovascular benefits, running is a great exercise because it releases endorphins.

Endorphins are feel-good hormones that lower stress and trigger a sense of well-being. Rather than sit around and ruminate over your date, getting out and doing something physical will help get rid of that negative energy so that you can enter the date confident and refreshed.

Tip #3: Don’t Put All Your Eggs in One Basket

You now have an idea of what to talk about on a first date. But do you still feel stressed? Is there a part of you that is dreading the potential letdown of things not working out with this person?

The problem could be that you’re putting all your eggs in one basket. You only focus on one person at a time. And when that’s the case, every facet of dating can become stressful. Furthermore, this type of dating strategy can lead to self-sabotage.

So what do you do? Choose a more effective dating strategy.

Give Them Something to Talk About: MegaDate

When it comes to what to talk about on a first date, how to act on a first date and overcoming first date jitters, here’s the thing — practice makes perfect.

One of the best ways to improve your first date conversation game and more is to start MegaDating.

What is Megadating?

MegaDating is a dating strategy that involves dating several people at the same time in order to diffuse energy by keeping your calendar full.

When you MegaDate, confidence increases and anxiety dissolves. This is because MegaDating allows you to see firsthand that there are plenty of fish in the sea. And when you view the dating world with an abundance mindset, you avoid things like:

• Settling for the mediocre
• Chasing after women
• Being relegated to the friendzone time and time again
• Getting hung up on “the one”
• Getting stressed out about dating

During my 100-date experiment, I use MegaDating as my main strategy. It helped me find a compatible, long-term partner and it can do the same for you.

Want to Learn More?

Let’s talk.

If you’re ready to get a lot more dates, attract tons of high-value, gorgeous women and stay out of the friendzone for good, head over to my calendar and book a 1-on-1 Skype session with me today!

No topic is off limits. During our session, we will address your dating roadblocks and create an action plan to help you overcome those roadblocks and CRUSH your goals. I’ve helped men across the world increase their self-esteem, amp up their appeal and attract tons of desirable women. I’d like to do the same for you.