The 21 Best and Worst First Date Questions You Could Possibly Ask

Some guys have a knack for first dates. They can seamlessly navigate conversations, so topics flow from one to the next without any lulls. They effortlessly balance talking about themselves while still learning about their partner. They’re charming, funny, and quick-witted. They just really have it down.

Then there’s the rest of us, who might need a little help on first dates when the prolonged silence with our partner sounds deafening. If you find yourself in a bind on a first date, not sure of what to say, here are 20 questions that should hopefully get you and your partner talking again. These questions aren’t the boring “What do you do for work?” They’re ideal questions to ask if you really want to get to know your partner. (We also provided three bonus questions of what to definitely not ask your partner.)

The Best Questions to Ask on a First Date

1. What’s been your favorite vacation?

Why it’s good to ask: Everyone loves going on vacation and talking about what they did that made it so great,” says Maria Sullivan, Dating Expert and VP of Dating.com. “Asking this question on a first date will open up a conversation about where your date has traveled and if you are both into the same types of vacation destinations.”

2. What’s your dream travel destination?

Why it’s good to ask: “Talking travel really works,” adds Amanda Bradford, founder and CEO of the dating app, The League. “In one study, 18% of couples on first dates who discussed travel wanted to go a second date. In contrast, less than 9% of couples who talked about movies wanted to go out again.”

3. What are you most passionate about?

Why it’s good to ask: “People love discussing the hobbies and pursuits they enjoy,” says Bradford. “If you want to know who someone is, find out what they love.”

4. Are you more of a morning or night person?

Why it’s good to ask: Some people are able to wake up at the crack of dawn while other are able to stay awake until the crack of dawn,” says Sullivan. “Asking your date this question will give you an idea of their daily schedule. For example, are they up early at the gym or up late binge watching their favorite shows?” This can help determine if you two are compatible with one another.

5. Who should play you in the movie of your life?

Why it’s good to ask: “This fun ‘what-if’ question caters to their ego—and the actor they choose clues you in on how they see themselves,” says Bradford.

6. What’s the most interesting fact you know?

Why it’s good to ask: People are full of interesting facts,” says Sullivan. “This is a fun question to ask to find out what your date knows, and you might even learn something new.” Additionally, everyone loves coming across as interesting. It’s great you’re giving your date the opportunity to do so.

7. Who did you see for your first concert?

Why it’s good to ask: “Music is a great date topic,” explains Bradford. “Prepare to be impressed that they saw Beyonce, or saddened that they saw Nickelback.”

8. What was the best day of your life?

Why it’s good to ask: “This question takes your date back in time to a big life moment that they’ll love reliving,” says Bradford. “It goes much deeper than surface-level chat, and this deeper dive makes you stand out from other guys this person has been going on dates with.”

9. What’s your favorite holiday?

Why it’s good to ask: This question can give you insight into your date’s religion based on the answer, which can be an important part of a relationship,” explains Sullivan. It also opens up to conversation about religion, which yes, could be a lot on a first date, but also might not be. You’ll have to gauge to see if you should take the conversation there.

10. What’s the best gift you’ve ever given someone?

Why it’s good to ask: “They’ll get to brag a bit while feeling very generous,” Bradford says. It’s also a big red flag if they haven’t given anyone anything.

11. What do you love most about your job/career?

Why it’s good to ask: “This question lets you talk about work in a positive, emotionally evocative way, rather than boringly asking, ‘So, what do you do?’” says Bradford.

12. What were you like as a kid?

Why it’s good to ask: “Sharing stories from childhood gives them a chance to be vulnerable by giving you a glimpse of their younger self,” explains Bradford. “You’re helping them connect with you and with their younger self.”

13. What does your ultimate favorite meal consist of?

Why it’s good to ask: “Who doesn’t love food?asks Sullivan. “This question will allow you to figure out what types of food you have in common and if things go well, it can even help you decide where to go on your second date.”

14. What’s your hidden talent?

Why it’s good to ask: “This allows them to show off while sharing a secret—and sharing personal secrets can build trust and connection,” says Bradford.

15. Would you rather…?

Why it’s good to ask: “A first date should be fun, and good ‘Would You Rather’ questions get your date laughing,” Bradford says. “A 2014 study found that women are drawn to men with a sense of humor. Here are some fun examples!” Bradford recommends:

“Would you rather have a snowball fight or a food fight?”

“Would you rather walk in on your parents having sex, or they walk in on you having sex?”

“Would you rather have eight arms or be a cyclops?”

16. What do you usually do on weekends?

Why it’s good to ask: This question gives you a chance to see if you have matching lifestyles. If your partner’s weekends consist of reading in bed whereas most weekends you’re out at the club drinking with friends, then they might not be the right person for you. If you do have similar weekends, then the conversation will naturally flow from there. For example, if you both like reading, you’ll be able to discuss your favorite books. If you both like going out, you can talk about your favorite bars.

17. What’s on your bucket list?

Why it’s good to ask: This question now only gives you a sense of your partner’s interests, it also provides great ideas for date number two. If you really like them after the first date, sky diving might not be that crazy of idea if that’s something they’ve always wanted to try out.

18. Want to share an embarrassing moment?

Why it’s good to ask: On dates, we try to present the best version of ourselves, as we should, but sometimes, it can get a little too serious and even start to sound a little “braggy.” This question helps you and your partner be vulnerable with one another, breaking down any facades.

The Worst First Date Questions:

1. Why are you single?

Why you shouldn’t ask: “Although this question may seem harmless, it may leave your date feeling awkward and unsure how to answer,” she says. It also can be read as an insult. In essence, you’re asking, “So what’s wrong with you?”

2. How many exes do you have?

Why you shouldn’t ask: “Asking this personal of a question on a first date can be a big red flag,” she says. “It is important to take your dates privacy into consideration and not ask anything that might make them feel uncomfortable.”

3. How much money do you make?

Why you shouldn’t ask: “Someone’s income is not an important piece of information for a first date and may make you seem like you are more interested in money than the actual person,” she explains. “Spend the first date asking questions that will allow you to learn more about your date’s heart, not their wallet.”

 

Thank you for reading my blog. Please read, like, comment, and most of all follow Phicklephilly. I publish every day.

Buy my new book, Angel with a Broken Wing is now for sale on Amazon!

Listen to the Phicklephilly podcast LIVE on Spotify!

Instagram: @phicklephilly    Facebook: phicklephilly    Twitter: @phicklephilly

11 Marriage Truths From Divorce Attorneys

The best source for marriage advice? Divorce attorneys. Before you protest, just think about it: Every day at work they see the types of marital problems that lead otherwise happy couples to split up.

With that in mind, we recently asked 11 family law attorneys to volunteer their best love and relationship advice. See what they had to say below.

1. A sustainable marriage is not about love, it’s about tolerance.

“Can you tolerate all your partner’s quirks? Even the ones that you don’t like, are they tolerable? Don’t marry your partner thinking that any of his or her quirks are going to change, improve or wane. As we get older, your partner’s quirks will only magnify. So if you can’t tolerate it now, you for sure are not going to be able to tolerate it in the future. Tolerance may not be romantic, but it is the key to a long lasting marriage.” — Melissa B. Buchman, an attorney in Beverly Hills, California 

2. Give your spouse the benefit of the doubt. 

“Unfortunately, many couples I see going through a divorce ascribe bad — or sometimes terrible — motives to everything their spouses do. What is the harm in assuming or presuming the best? Even if you’re wrong, it hurts no one. And it may be the start of a better relationship.”  — Randall M. Kessler, an attorney based in Atlanta, Georgia

3. Don’t be afraid to feed your spouse’s ego now and then.

“Silly as it may sound, your spouse wants to feel strong, sexy and attractive. I have seen spouses cheat because someone else showed them attention and made them feel good.” — Christian Denmon, an attorney in Florida 

4. Put your spouse before your kids. 

“This may not be the most popular piece of advice, especially for parents, but after watching countless people get divorced because they allowed themselves to slowly drift apart over the years, I honestly believe it’s true. We are all busy these days. It’s far too easy to put your job, your house, your activities and your kids before your spouse. Don’t do it! While many people believe that their kids have to come first, if they don’t put their spouse first and their marriage eventually sours, it’s not going to be doing the kids any favors. If you value your marriage, choose to put it first.” — Karen Covy, an attorney and divorce coach based in Chicago, Illinois 

5. Don’t wait until it’s too late to work on your marriage.

“Work on your marriage while it’s still a good marriage, don’t wait until there’s a problem. ‘Work’ does not have to mean counseling, it can simply be having a set date night once a month.” — Carla Schiff Donnelly, an attorney based in Pittsburgh, Pennsylvania

6. When you need to discuss something important, timing is everything.

“When making a request, decision, criticism or apology, it’s crucial to do it when and where your spouse is at their best: after working out, perhaps, or on Friday night, or after a glass of wine or early in the morning before the kids are up. Ask yourself: Is this really the most constructive setting for my partner to hear what I need to bring up? I marvel at stories from clients about how they tried accomplishing something regardless of their spouse’s readiness to receive it and how shocked and dismayed they were when they got rebuffed or ignored. Bringing stuff up on a Sunday night, for instance, when you know he or she gets the back-to-work blues — or right after work, when you’re both exhausted? Bad idea.”  — James Sexton, an attorney based in New York City

7. Know that you can’t change your partner.

“My piece of advice mirrors a quote from Maya Angelou: ‘When people show you who they are, believe them.’ In other words, many of us have this deep-seated desire to change our partners, especially women. This can manifest itself in actions like trying to get them to wear neutral colors instead of bold plaid shirts or attempting to change them from boring in bed to hot in the sheets. The bottom line is, we are who we are and either we accept it or go back on Match.com.” — Lisa Helfend Meyer, an attorney in Los Angeles, California

8. Love is about the little things.

“Marriage is work but worth the effort. Go on dates, speak one another’s love language and cherish the little things. Remember that love looks and feels very different as your relationship changes and evolves.” — Natalie Gregg, an attorney in Allen, Texas  

 

Thank you for reading my blog. Please read, like, comment, and most of all follow Phicklephilly. I publish every day.

Buy my new book, Angel with a Broken Wing is now for sale on Amazon!

https://www.amazon.com/s?k=charles+wiedenmann&ref=nb_sb_noss_1

Listen to the Phicklephilly podcast LIVE on Spotify!

Instagram: @phicklephilly    Facebook: phicklephilly    Twitter: @phicklephilly

ANGEL WITH A BROKEN WING: Inspiration and Behind the Scenes – Part 1

The truth behind the story!

This is a 4 part mini series I wrote over the weekend as a companion to my recently published book. It will run over the next 4 weeks, every Monday morning at 8am!

Thank you!

Angel with a Broken Wing is my first work of fiction. It’s got all of my favorite elements in it. But where do these ideas come from? Well, I’m going to tell you.

I’m going to think back and try to remember some of the inspiration for this story.

I am obviously Christian Blackmore. Not anymore, but I was back in the 90’s. I was miserable in my marriage and my job, and I wished  I could just run away from the life I had created.

The Cover: I was an art major all through school. When I think about that now, it feels like a million miles away. I liked comic books growing up, and my first exposure to art was in comics. I always made art throughout my childhood, so art class was a natural progression for me in school. It was the only class that was effortless.

I loved to work in pen and ink. I liked its stark simplicity. I have several works from high school that I still retain in my collection. This one, The Angel is my favorite.

It was an incredibly cold day in February of 1980. I was in my double period, art major class. There were only two of us in the class that were any good. Me and Bill Polini.

I looked out the window as the snow came flying. I took pen in hand, and imagined a beautiful girl. In a warm place. She’s with me. We’re maybe riding horses…or camels. She turns to look at me, and the reflection of the oasis behind me reflects in her sunglasses. I long to kiss her.

“Yea. I should try to draw that.”

Uncle John: I had an uncle John on my mother’s side of the family. I share many of the same characteristics of my mom’s side of the family more than my dad. My mother had four brothers; Roland, Robert, Norman, and John. All of her brothers kept their hair and all died in their late 70’s and 80’s so maybe if my liver holds up, I’ll meet the same fate. John never left me any inheritance, but my uncle Rob left all of us kids some loot and it was substantial. He lived in Florida.

The Pinto: My grandmother, (My dad’s mom) We called her Grammy. I loved her. When everybody thought I was a piece of garbage in my early teens, she was the only one that had faith in me. So She will always have a special place in my heart. She was a cool lady, who liked a cold glass of beer and some good neighborhood gossip. Just an adorable lady. When she died, the last car she owned was a gold Ford Pinto. That car is my last memory of her. So I used it in the story. The car’s fate is based on stories I heard back in the 70’s about an engineering flaw in the vehicle.

Woodbury, New Jersey: I lived in Woodbury from 1992 to 2001. My wife and I owned a house on Barber Street. I modeled Christian Blackmore’s residence after my own house there. So when I wrote about him in his house in Woodbury, I could picture my own life there.

The Phoenix: I remember first hearing about the story of the Phoenix on an old record album. It was a collection of stories about superheroes. It was like an old radio show type collection of plays on one LP. I remember hearing about the Phoenix in one of those stories, probably back as far as 1973. When one of the characters describes the Phoenix, it is a verbatim rendition of what I heard on that record, nearly 50 years ago. I always felt like I could relate to the Phoenix in my own life. I always felt that no matter how many times I got destroyed in my life, I always came back better than what I was before. I think that’s why I have the characters make a stop over in Phoenix, Arizona on their journey to LA. There are some transforming moments for a few of them in that chapter.

Gloucester County College: When I was married back in the 90’s my then wife came from a very collegiate family. I never went to college, but had several college credits from the American Institute of Banking through courses I had taken through the bank I worked for. My wife thought I should go back to college at night and take courses to get my college degree. So I did. I took those classes at night after work, at Gloucester County Community College. I don’t feel that it was a waste of time, because it led to some interesting things. I’ll be getting to them shortly.

The Gun: Everything you read in Angel about the Bulldog .44 revolver is true. I never owned a gun, and like Christian Blackmore, I hate guns. But all of the info about that weapon is from real events. The story Christian tells Sheryl about the girl at the shore is all true. That happened to me in the summer of 1977. Funny thing is, I recently reconnected with that girl from New York on Facebook. (At 57, she’s still hot!) Oh, one last thing, I had to make a slight change in the action sequence involving that gun. During the final edits of the book I discovered that the bulldog .44 only holds 5, not 6 bullets like most revolvers! I guess because those bullets are so big!

Sheryl Stanton: Sheryl was inspired by a girl I met in one of the banking courses I took at Gloucester County College. I pretty much describe Sheryl as how this girl was in real life. We had a good friendship for a brief period and even had some romantic dalliances. She did break it off with me when she moved to California for a period of time. The real Sheryl never worked in a mental health facility. That’s completely made up for the story.

Karl Itzky: The first kid I met when I went to Frankford High School in 1978, was a guy named Karl Itzky. He was the only person I knew other than my older sister. I just liked his name. He is nothing like the Karl Itzky in the book. He was a nice guy, who I sadly lost touch with when I moved up the social ladder in high school.

Honest Files: The name of the bar/restaurant where Christian and Sheryl hang out is taken from a song by the band, Urge Overkill. There are many references in the book about music I was listening to back in the 90’s where this story takes place. It’s from their album, Exit the Dragon. Here are some of the lyrics from the song:

Hey, hey I’m dead on arrival
Hey, hey I’m distant
Crawling right back
Yes, I’m crawling right back
‘Cause I’m honesty, don’t break my heart
Honesty won’t break it
Honesty won’t break you heart
Honest it won’t
It won’t, it won’t, it won’t, it won’t, it won’t…

I thought it was a cool song, and that bar is where I hung out with the real Sheryl back then. It’s where we would spill our guts to each other about everything in our lives. I used to say we were opening the ‘Honesty Files’ about what we were experiencing at that time.

The real place is exactly the way I describe it in the book. The animal trophies on the walls, all of the real bookcases all around the room, and the fireplace. We spent many a night there pounding martinis and smoking tons of cigarettes. (Yea, you could smoke in restaurants and bars back then!) It was a welcome repose from our chaotic lives.

Exterior - Picture of Charlie Brown's Steakhouse, Woodbury ...

Here’s the real Honesty Files… It’s a place called Charlie Brown’s at 111 Broad Street, in Woodbury, NJ

 

More next week!

 

You can buy Angel with a Broken Wing on kindle and paperback right here:

 

https://www.amazon.com/s?k=charles+wiedenmann&ref=nb_sb_noss_2

 

 

 

Thank you for reading my blog. Please read, like, comment, and most of all follow Phicklephilly. I publish every day.

Buy my new book, Angel with a Broken Wing on Amazon!

Listen to the Phicklephilly podcast LIVE on Spotify!

Instagram: @phicklephilly    Facebook: phicklephilly    Twitter: @phicklephilly