First Date Questions to Banish Awkward Silences (Rejection Proof)

First Date Questions to Banish Awkward Silences (Rejection Proof)

A first date can be nerve-wracking. There are almost certainly going to be some anxious feelings associated with any first date. There is one thing for sure that I’m almost positive all of us can agree on.

The dreaded awkward silence is our worst nightmare.

It’s one of the most common, and worst things about a first date. Anxiety for both parties is almost a given on a first date. It’s also very stressful knowing how important first impressions are, and trying to come off as “perfect” as possible- especially when no one is perfect!

MORE: 50 Great Questions To Ask A Guy

To me there is truly nothing worse than the dreaded feeling of the silence getting longer and longer, while your anxiety worsens and worsens. You begin to think, “Say something! Somebody! Anything!”

Well with these questions, that somebody can be you!

I’ve dealt with having awkward silences before and have found the best way over the years to have it never happen again. What I have found is the best solution is to have a repertoire of questions to fall back on if it ever becomes awkward.

These questions are a great way to keep the conversation going and avoid those terrible silences. I’ve learned that just a few questions will break that initial tension and will usually spiral into a great dialogue!

Once the anxiety is gone, and you gain some comfortability, a first date can become a great experience!

>MORE: Ask A Guy You Like These 20 Cute, Amazing Questions

With enough good experiences, that anxiety and fear will slowly start to melt away. I’ve always found out the more comfortable and secure I am the less anxious I feel in my personal interactions. Its best just to be yourself- don’t try to fit any mold!

You want a guy that wants the real you!

Categories Of Questions You Will Receive in this Article:

Take The Quiz: Does He Like You?

Click here to take our quick (and shockingly accurate) “Does He Like You” Quiz right now and find out once and for all if he likes you…


Safe First Date Questions:

These are simple and harmless, and perfect for breaking the ice! There is nothing here to forward or awkward!

What do you do for a living?

Do you enjoy your job?

How often do you work?

Do you enjoy going out a lot?

What’s the best party you’ve ever been to?

Favorite character from a movie or show?

Do you have any hobbies?

Favorite way to de-stress?

Any siblings?

Favorite music?

Favorite movie?

MORE: Ask A Guy You Like These 20 Cute, Amazing Questions

Do you like horror movies?

What do you think about social media?

Any funny family members?

What did you study?

Where did you go to school?

Favorite class?

What’s your longest Netflix binge?

Were your parents strict?

The most boring thing in the world to you?

What’s the most exciting thing?

What would you have to get paid a million dollars to do?

What’s your favorite tv show?

Are you a night owl or an early bird?

Do you have any allergies?

Favorite color?

Would you rather go to the beach or the mountains?

Do you play video games?

Do you like to play board games?

Card games?

MORE: How To Never Run Out of Things To Say On a Date

Do you have any pets?

How often do you drink coffee?

What’s the longest car drive you’ve ever been on?

Have you ever been somewhere exotic?

Have you ever done anything “extreme” like parachuting or bungee jumping?

What’s your favorite animal?

Do you know any jokes?

What’s your favorite motorsport?

Train or fly?

Favorite foreign culture?

Favorite sport?


Interesting First Date Questions:

These are for when you are more comfortable with someone; maybe after a few drinks, when the conversation is flowing and you’re getting to know each other better.

Proudest moment of your life?

Do you believe in extraterrestrial life?

Have you ever been in a car accident?

Biggest regret?

Worst fear?

Most embarrassing moment?

Were you ever bullied?

Weirdest first date experience?

MORE: Random Questions To Ask A Guy

Do you believe everything happens for a reason?

Do you like any super weird things no one knows about?

Happiest you’ve ever felt in your life?

Who is the most intriguing public figure in the world alive to you?

Who is the most influential person of all time to you?

If you had 24 hours to live, what would you do?

If you died tomorrow, what would you regret?

Do you believe in life after death?

Do you like drinking?

Have you ever known anyone with substance abuse problems?

Favorite vacation?

Any weird songs you love but don’t want to admit to loving?

Weirdest friend you have?

Do you get along with your parents?

Where do you see yourself in 5 years?

What kind of kid were you in high-school?

Have you ever been injured?

MORE: 225+ Amazing Questions to Ask a Guy: The Ultimate List

Where would you live if you could live anywhere?

Would you rather be poor and happy or rich and depressed?

Biggest lie you’ve ever told?

Craziest thing you’ve ever done?

Ever gotten away with something bad or illegal?

If you were animal what would you be?

Would you ever join the armed forces in a time of need?

What’s your view on law enforcement?

Do you think people need “safe spaces”?

If America were to fall into total anarchy tomorrow what would be the first thing you would do?

If you were ever arrested what would be people’s first suspicion?

What’s the scariest experience of your life?

What’s your dream car?

If you were president what is the first law you would enact?

If you had to kill one to save many could you do it?

If you could have any job what would it be?

MORE: 20 Questions to Ask a Guy You Like to Get Closer

Would you ever work for the government in any form?

What’s your view on police?

Do you have any unorthodox beliefs?

What was the best concert or show you’ve been too?

If you were in a job position with very important top secret information would you release information to those around you to protect them?

Would you rather own a boat or a plane?

If you could only play one sport for the rest of your life what would it be?


Flirtatious/Sexy First Date Questions:

Do not be too forward and jump into overtly sexual questions in the very beginning! Play it safe, see how comfortable you get! These are some flirtatious ones to “spice things up”.

How often do you think about sex?

Do you think men and women can be friends?

Who do you think the hottest celebrity is?

Have you ever made out to music?

When the last time you got with someone?

What’s your perspective on “50 shades”?

Have you ever had a celebrity crush?

MORE: What First Date Questions Should You Ask To Break The Ice?

What are your biggest turn ons?

What are your biggest turn offs?

Craziest thing you’ve done sexually?

Do you have any kinks?

Do you have any fantasies?

What’s the most attractive thing to you about women?

Do you like boobs or butts?

Have you ever been caught watching porn?

What kind of porn do you watch?

What’s the most embarrassing thing you have ever been caught doing?

If you had the opportunity to do anything to a girl what would you do?

Do you like foreplay?

Have you ever owned a sexual toy?

What’s your favorite body type?

What was your first experience hooking up with someone like?

Would you ever get with someone of the same sex?

Have you ever been caught naked before?

Have you ever given a massage before?

Have you ever sent anyone dirty photos?

Have you ever “sexted” anyone before?

MORE: 5 questions to ask on a first date if you want to really figure someone out

Are you more dominant or passive?

Rough or passionate?

Do you like it when women wear lingerie?

What’s the sexiest thing a girl has ever done to you?

Have you ever recorded anything?

Boxers or briefs?

Have you ever had friends with benefits?

What’s the longest you’ve gone without sex?

Have you ever had a lap dance?

Favorite place to kiss a woman?

Last time you had a wet dream?

How many sexual partners have you had in your lifetime?

What’s your favorite position?

Do you like roleplay?

Have you ever watched porn with a girl?

Have you ever been so turned on you couldn’t control yourself?

Just remember, be comfortable and have fun. A first date certainly can be a bit stressful, but with confidence, and a rolodex of questions to ask you’ll have no problem with keeping the conversation going. With good conversation comes that instant relief. The more you talk the more comfortable you become!

It’s always important to note that we are all totally different and react to different things in a multitude of ways.

I’ve had first dates, where everything was fine, but for some reason I just didn’t feel fulfilled in any sort of way, like no ground was broken. While I’ve had others where it seems like I’ve known the girl my entire life- with no change to myself.

Sometimes it’s just a great fit! Some people are just meant for one another!

It’s not your or their responsibility if you aren’t cohesive, it’s simply just not a natural fit.

The more you talk the more you get to know someone, and the closer you inevitably will become! These questions will keep you talking and also help you learn some good information about the person you are interested in to aid in furthering your relationship!

There are 2 big turning points every woman experiences in her relationships with men and they determine if you end up in a happy relationship or if it all ends in heartbreak.

So pay attention because the next step to take is vitally important. At some point he’s going to ask himself if you are the woman he wants to commit himself to for the long term…

Do you know how men determine if a woman is girlfriend material (the type of woman he commits himself to) or if he sees you as just a fling? If not, you need to read this next: The #1 Thing Men Desire In A Woman…

And the second big problem many women face: Do you feel he might be losing interest, going cold emotionally or pulling away? If so, then you need to read this right now or risk losing him forever: If He’s Pulling Away, Do This…

Want to find out if he really likes you? Click here to take our quick (and shockingly accurate) “Does He Like You” Quiz right now and find out once and for all if he likes you…

Take The Quiz: Does He Like You?

30 comments… add one
  • stella July 5, 2018, 10:04 pm

    great! now i can put an end to uncomfortable awkward silences! you did a great job in sharing this post!

  • angela July 4, 2018, 6:34 pm

    now i am aware on how to break awkward silences during first dates. hope my date will find the topics or the conversation good and interesting.

  • ximena July 3, 2018, 7:18 pm

    wow! these will definitely lead to a good conversation! i will list these questions down to avoid awkward silences and to help me keep the conversation flowing.

  • aurora July 2, 2018, 8:43 pm

    i will never forget my first date! i was anxious, shaking and my bladder is giving me false signals that i have to pee! awkward silences were there too! haha

  • veronica June 29, 2018, 7:48 pm

    i’ve been waiting for this article my whole life! thanks for sharing! it’s definitely a big help!

  • micaela June 29, 2018, 2:50 am

    i like visiting your site. my day is not complete without reading one of your articles!

  • betty June 27, 2018, 8:32 pm

    awkward silences are the worst! i’ve been on a date full of many awkward pauses and it felt like the time seems to drag on forever!

  • eugene June 26, 2018, 7:22 pm

    these are nice questions! i hope you can post an article about questions that should not be asked on a first date too.

  • allison June 25, 2018, 8:38 pm

    i always find myself scrambling for something interesting to say whenever i go out on a date and i hate it! i don’t want my date to get turned off so i try to avoid awkward silences although sometimes, it is really uncontrollable.

  • marjorie June 22, 2018, 6:01 pm

    awkward silences are really uncomfortable for everyone not just during a first date. it is nice to know that there are articles like these that we can use to beat this and get the conversation back on track.

  • matilde June 21, 2018, 7:56 pm

    i don’t know what to talk about when i am out on a first date and i don’t want to experience awkward silences! glad i came across this post! i can use these questions!

  • keeva June 20, 2018, 6:10 pm

    i went on a date last night and the first topic we talked about was his scariest experience and guess what, we didn’t notice that we were sharing stories for about 2 hours already! great topics really do kill awkward silences.

  • snow June 19, 2018, 6:16 pm

    i always try to come off as perfect as possible during first dates because the first impression is important. that is possible with the use of these first date questions! if my date can’t bring out topics to talk about, i will use this list.

  • desiree June 18, 2018, 6:21 pm

    first dates are really nervewracking but exciting. you can’t avoid awkward silences but just in case the conversation runs dry, you can definitely use some of these questions.

  • cheryl June 15, 2018, 9:08 pm

    i think awkward silences are normal on a first date.. just saying.

  • beatrice June 14, 2018, 9:29 pm

    you will never have to be scared of awkward silences anymore when you go on a first date! thanks for this superb article!

  • madison June 13, 2018, 5:17 pm

    i will never forget our first date! he was so turned on to me and could not control himself! we always laugh whenever we reminisce and talk about it.

  • amber June 12, 2018, 6:54 pm

    these are really nice questions. they are open-ended and great conversations starters. with these, you can really break silences during a first date.

  • coleen June 11, 2018, 5:22 pm

    i don’t want to scare my date away because of an awkward pause. these first date questions are good. i will take note of these.

  • mia June 8, 2018, 5:49 pm

    it is very interesting to ask Sexy or Flirtatious questions on a first date but i should know how to play it safe. hope my date is comfortable talking about sexy topics.

  • jilll June 7, 2018, 5:20 pm

    well, for me, it is natural to experience awkward silences, especially on a first date. whenever that happens to me, i just think of questions about any popular topic that i know most people will have something to say.

  • kathleen June 6, 2018, 5:33 pm

    you should be able to keep a conversation going if you take time to break these questions down. appreciate you sharing this.

  • karen June 5, 2018, 7:23 pm

    thank you for this list! shy girls like me need this one! you are really a great help!

  • brittany June 4, 2018, 8:02 pm

    my best friend shared this post to me because i told her that my crush asked me out for a date. i memorized every detail and guess what? i never run out of things to say! haha!

  • donna June 2, 2018, 3:37 am

    i love this article! there will never be any nerve-wracking dates for me, ever! with these great questions, my date will surely have a good first impression on me.

  • doreen May 31, 2018, 4:59 pm

    the questions in this article really work! i tried it and there were no awkward silences ever when we had our date last night! i highly recommend this site! you will learn a lot.

  • alicia May 30, 2018, 4:36 pm

    can these questions really banish awkward silences? i will go on a first date tonight with a guy that i really like and i will use some of these questions.

  • gail May 29, 2018, 3:21 pm

    fantastic! i will absolutely use these fantastic questions when i go on a date. i will never allow an awkward silence to kill my promising first date again!

  • sam May 25, 2018, 7:25 pm

    i will not forget my first date! It was very uncomfortable at first but when my date started talking, we both had a good time!

  • lucy May 24, 2018, 3:06 pm

    i love these ideas so much! i’m so glad i saw this post, i will take note of all these and make sure to use them. i have a date tomorrow and i’m so nervous but excited too!

Leave a Comment