logo
episode-header-image
Nov 2022
1h 18m

E498 Ask Nick - Matchmaking Gone Wrong

Nick Viall
About this episode

Welcome back to another juicy and exciting episode of The Viall Files: Ask Nick Edition! We’re back again to bring on our callers and give them advice on their situations. We bring on our first caller who set up two friends on a date. After hearing feedback from one of her friends that the guy gave off a lot of icks, she wonders how she can tell her guy friend to improve himself as a dater. Next, we talk to someone who has a medical condition which makes sex painful. She wonders when is the best time to talk about it and how she can give the people she dates an ‘out’ if it’s a deal breaker. Our last caller wonders if she unintentionally put herself into the hookup zone. Now she learns to understand what this guy really wants and how to be direct with what she wants herself. 

“I’m the Nick Viall of my friend group!”

If you are interested in running a book club in your city, send an email to: DTYEHBBookClub@gmail.com 

Please make sure to subscribe so you don’t miss an episode and as always send in your relationship questions to asknick@kastmedia.com to be a part of our Monday episodes. 

Pre-Order Nick’s Book: https://www.abramsbooks.com/product/dont-text-your-ex-happy-birthday_9781419755491/

Support a Local Bookstore: https://bookshop.org/books/don-t-text-your-ex-happy-birthday-and-other-advice-on-love-sex-and-dating-9798212185622/9781419755491

Check out our new "Introvert" merch at http://www.viallfiles.com today!

If you would like to get some advice on Office Hours send an email to asknick@kastmedia.com with “Office Hours” in the subject line! 

THANK YOU TO OUR SPONSORS:

Canva: Design like a pro with Canva Pro! Right now, you can get a FREE 45-day extended trial when you go to https://canva.me/viall.

Total Wireless: Total by Verizon is available at http://totalbyverizon.com/ and at retailers nationwide.

Caraway: Visit http://www.Carawayhome.com to take advantage of their Cyber Season Event and score up to 20% off your next purchase of non-toxic kitchenware. This deal won’t last long, so visit http://www.Carawayhome.com to shop all their incredible products for up to 20% off this holiday season. Caraway.

Match Dating App: If you Do You — you already know the best relationships show up when you show up for yourself first. There’s never been a better time to try Match. Download the Match app today. 

Episode Socials:  @viallfiles @nickviall

See omnystudio.com/listener for privacy information.

Up next
Yesterday
E963 – Going Deeper with Kaja Sokola
Welcome back to The Viall Files: Going Deeper edition. Trigger Warning: This episode includes content pertaining to sexual assault. Please listen at your own comfort. On June 11th, 2025, jurors acquitted Harvey Weinstein of sexually assaulting Kaja Sokola. However, Weinstein was ... Show More
1h 18m
Jul 8
E962 - Next Gen NYC w/ Gia Giudice, Love Island USA, Cierra’s Exit, Mormon Wives Reunion & Bach In Paradise
Welcome back to The Viall Files: Reality Recap! Sunday night’s Love Island was one for the books. Cierra was dumped, the rise of Nicolandria, Amaya Papaya beginning her reign as It Girl of the villa, and that’s just one episode! We recap all that AND more from the past week. Also ... Show More
1h 26m
Jul 7
E961 Ask Nick - Is My Pastor Dad A Scammer?
Our first caller is debating giving her dad $125k. Our second caller is wondering if her boy roommate is a red flag. And, our third caller wants to know if she should give her embryos frozen or donate them. “You’re not going to get better, by not doing." Listen to Humble Brag wit ... Show More
1h 32m
Recommended Episodes
Jun 2024
Are Assumptions Ruining Dating?
Do we actually know what the opposite sex wants when it comes to dating, or have we been wrong all along? On this episode, we’re discussing a recent study that shows how assumptions and misconceptions could be hurting your dating life. We talk about why and how we misread people ... Show More
1h 15m
May 2024
Don’t Wait for a Partner to Do the Damn Thing!
If you feel like everyone around you is partnered up and you’re missing out on doing things because you’re single – this episode is for you! We are encouraging you to live the life you want (and deserve) regardless of your relationship status and are giving tips for doing it – ev ... Show More
1h 34m
Jun 2024
Falling in Love With Your Friend feat. Ali Kolbert
We are so excited to welcome back our friend and hilarious comedian Ali Kolbert, this time with her girlfriend Lauren! They are sharing their friends-to-partners love story and how you know when a relationship is The One. We are also discussing ending engagements when you know it ... Show More
1h 24m
Jun 2024
Remi and Cal’s Engagement Party
This week on Pretty Basic, Alisha sits down with Remi and her fiancé, Cal, for a juicy and revealing episode you won’t want to miss! Get ready as Alisha grills the couple with both fun and serious questions about their relationship, delving into all the spicy details.We play a wi ... Show More
1h 5m
Jun 2024
Your Summer Dating Strategy with Jared Freid
Our good friend and fan fave Jared Freid is BACK with all the info you need to know for a successful summer of dating! We talk about why meeting IRL is the move, but how do you do it? Where are the single guys hanging out? What time of day is best to meet someone? How do you maxi ... Show More
1h 52m
May 2024
How Romantic Socialization Has F*cked Us Up with Kara Loewentheil
It’s not you…it’s the brain gap. In this eye-opening episode with author/life coach/podcaster Kara Loewentheil, we’re unpacking what the brain gap actually is and how it f*cks you up when it comes to your love life, body image, and more. Kara educates us on the four traps of roma ... Show More
1h 33m
Jun 2024
The Snack: Chipotle Boys, TikTok Therapists, and Summer Reading
Welcome back to The Snack – a lighter serving of Girls Gotta Eat. This week, we’re talking about (in order):  Nick Cannon wants gifts for Father’s Day Sabrina Carpenter and Barry Keoghan Real Housewives drama (NJ reunion being canceled) Which reality shows Rihanna and Kim K. watc ... Show More
50m 46s
Jun 2024
Country Clubs and Sex Toys with Heather McMahan (and Jeff)
We could not be more excited for our Dear Media debut with fellow Dear baddie Heather McMahan! We’re discussing her red carpet reporting (with some tea), how LA makes you feel fugly (but is temple filler the answer?), and what her next Netflix special is about. Then we bring in H ... Show More
1h 15m
Jun 2024
Sabrina Zohar's No Bullshit Advice for Modern Dating, Healing Toxic Relationship Patterns, & Authentic Communication
Everyone's favorite entrepreneur turned no-bullshit dating coach Sabrina Zohar is here to drop some major truth bombs about what many people are getting wrong in relationships by playing games and avoiding the real work. Sabrina shares insights from her own dating journey and mis ... Show More
55m 47s
Dec 2023
The Difference Between A Wedding And A Marriage ft. Rabbi Steve Leder
On today’s episode, I sit down with Rabbi Steve Leder. Rabbi Leder is an incredible author and thought leader, and he served as the senior Rabbi of Willshire Boulevard Temple before recently stepping down. We discuss why he proposed to his wife on their second date, what he has l ... Show More
1h 14m