Online Dating Tips: Holiday-Based Conversation Starters to Try

happy man using smartphone

Are you giving online dating a try this holiday season? You may find yourself nervous and unsure about how to start a conversation with someone. Maybe you’re getting ready to send that first message, or have decided to meet up with someone for a first date.

A 2016 study found that the single most important trait single people look for in a new relationship is “meaningful conversation.” But the study also revealed that 60% of respondents said it’s possible to grow more in love after just one good conversation. So what does all of this mean for your holiday conversations in person and online this year?

Good conversations during the most wonderful time of the year

Coming up with that opening line can be tough and intimidating. If you’re meeting people through online dating, you may worry if your message will get lost in someone’s crowded inbox. But the holidays offer great opportunities to start meaningful conversations that will spark someone’s interest.

Whether you’re meeting up with an old friend from high school while you’re back home or you’re reaching out to someone online, here are some great conversation starters for you to try out this holiday season!

Online dating tips: 33 holiday-based conversation starters to try this year

1. What’s your favorite holiday?

Even though you’re surrounded by Christmas trees and stockings hung by the fireside, Christmas may not be your date’s favorite holiday at all. Maybe they’d rather be celebrating Thanksgiving again, or pulling out their Halloween costume. Don’t forget to share your favorite holiday in return!

2. What is the first thing that comes to mind when you think of Christmas?

Maybe when they think of Christmas, they stir up memories of opening gifts at their grandparents’ house. Or perhaps Christmas brings to mind the way they delivered cookies to neighbors as children. If you want to get to know someone you’ve met via an online dating service or in person, this is a great question to start conversation about their favorite memories.

3. When was the first time you became aware of God’s love for you?

Christmas is the celebration of the moment when Christ took on our humanity and became man. That’s an incredible act of love. In fact, it’s the ultimate example of sacrificial love for us here on earth. When you use this conversation starter, you’re starting a deep, meaningful conversation about your faith experience. If sharing faith and values is an important part of your discernment, this is a great conversation starter for you!

4. What’s one of the most memorable gift-opening moments from your childhood?

Did they get a puppy when they were young? Maybe the bike that they saw by the Christmas tree is their best memory from childhood holidays. This question can be a fun trip down memory lane with someone, and it can also tell you a little bit about their family of origin!

5. What is a Christmas song that makes you cringe?

Not everyone likes “Rudolph the Red-nose Reindeer” or “Silent Night.” Have a fun laugh about the songs that you both can’t stand when the holidays come around.

6. What is the best gift you ever gave someone?

It’s better to give than to receive! You can get to know a lot about someone by the way that they give. Maybe they love shopping for that intentional gift, or giving the gift of quality time with those they love. This can be an especially fun question to ask someone if their favorite way to show love to those around them is through the love language of gift-giving!

7. What is your favorite holiday song?

So you’ve talked about the songs you both can’t stand. Now it’s time to talk about the songs that make you crank up the radio during Christmas time.

8. What kind of holiday shopper are you?

Does the person you met via online dating thrive on Black Friday? Maybe your date is a Christmas Eve shopper (we’ve all been guilty of that at one point or another, right?). Or perhaps they love planning ahead all throughout the year, picking up gifts as they see them, even if it’s July! Asking this question can teach you a lot about how this person plans for big events in their life, too.

9. What is the ugliest Christmas ornament you’ve ever seen?

We’ve all seen that one ornament or Christmas decoration that made us cringe. Have a good laugh about some of the tackiest holiday decorations you’ve seen before.

10. If you could be a character in a holiday movie, who would you be and why?

Maybe this holiday season has left them feeling like the Grinch. Or maybe the Christmas season leaves them filled with joy and laughter like Buddy the Elf or Clark Griswold.  This question can tell you a lot about their feelings towards the holidays this year! Don’t forget to share your holiday character lookalike with them, too.

11. What is the one food item you have to hide from yourself during the holidays?

The holidays are full of great food. Maybe the person you’re getting to know could survive on turkey leftovers alone. Or they have to make sure they don’t get stuck with the Christmas cookies at their house or those sweets won’t last long. Get to know what their favorite foods are! Then, go deeper by asking about why they enjoy those foods, or if there are good memories from their past associated with their favorite foods.

12. Finish this thought: “It wouldn’t be Christmas without . . . “

Grandma’s house? A fire in the fireplace? A warm cup of cocoa? Family reunions? The possibilities are endless with this question.

13. If you could pick one place to spend the holidays, where would it be?

If the person you’re getting to know through online dating lives in a place without any snow, maybe they’d like to spend one Christmas season up north! Or maybe the cold makes them cringe and they’d rather be relaxing at the beach with a Christmas-themed cocktail.

14. What is your favorite holiday road trip memory?

Learn about their family’s Christmas traditions with this question. Or maybe, they’ve moved away from home recently and the trips back to their hometown are their favorite.

15. What is the best Christmas gift you’ve ever received?

A great follow up to this question is asking the person you’re getting to know what made that gift especially memorable.

16. What is your favorite way to prepare for Christmas in Advent?

If you’re chatting with someone before December 25th, it’s a great time to ask them about their favorite Advent traditions.

17. What holiday dessert describes your personality?

Maybe their an ice cream enthusiast or a cake claimer. What do they think their favorite Christmas sweet says about them?

18. What outdoor winter activity do you love?

Snowboarding, building a snow man, having snowball fights . . . the list goes on and on! What are some of their favorite holiday activities to do in the great outdoors?

19. What is your least favorite holiday food?

If they’re anything like me, they can’t stand sweet potatoes with that sticky, sweet marshmallow topping. But maybe their least favorite food will be a total surprise!

20. If you could choose your age forever, what would it be and why?

If someone had great Christmas memories as a child, they may wish they could recapture that magic again.

21. What are three things on your holiday bucket list?

Their answer to this question could lead to a great opportunity to ask them out on a date if you haven’t met them in person yet.

22. Which celebrity would you want to have as a friend, and what would you buy them for Christmas?

Would they give Oprah Winfrey their favorite book, or share their Christmas cookies with Meryl Streep?

23. If you could design your own ugly Christmas sweater, what would it look like?

Those ugly Christmas sweaters have gotten more popular each year! Learn about their sense of humor with this fun question.

24. Which holiday would you want to add to the calendar?

Maybe they’d love to celebrate their love of baseball, traveling, or good food with a national holiday. Learn about their passions with this conversation starter.

25. Who is most likely to give you a gift as an inside joke? What is the gift?

If you want to get to know about their friendships with those they love, ask this silly question. You’ll get to hear the inside story to a fun moment of their lives.

26. What’s the most unique family tradition you celebrate during the holidays?

Is their family the kind of family that all runs a 5K before Christmas dinner? Maybe they

27. What are your New Year’s resolutions this year? 

If you’re getting together with someone after Christmas is over, this is a great time to talk about the year ahead! Don’t forget to share your resolutions with them, too. Maybe it includes asking them out on a date!

28. Which store would you never want a gift from?

This can be a fun conversation to have if you’re talking about their Christmas shopping habits.

29. If you could have one Christmas wish granted, what would it be?

Some may ask for a calm week at work, others for good friends. You can get to know someone new with this question! Don’t be afraid to go deeper in conversation based on their answer.

30. If you could start a charity or non-profit, what would it be?

What are their passions? Maybe they’d work with women and children. Perhaps they have a non-profit that they already are involved with that they’d be excited to share with you about.

31. How do you celebrate Christmas?

Maybe they get up early in the morning to open up gifts with family. Or maybe they sleep in after hitting up a Midnight Mass in their area!

32. What are some of your favorite Christmas books?

They could love the classic Christmas story found in the Gospels, but they may surprise you with a great book recommendation to put on your to-read list during your holiday down-time.

33. What do you think the best way to spend a Saturday in December is? 

This is a great question to ask! Remember their answer since it could come in handy when planning a first or second date.

Put yourself out there during the holidays!

The holiday season is a great time to meet someone new! “Everybody starts their New Year’s resolution, and a lot of times it’s: Get online or go out more, proactive stuff to really meet somebody,” said Jess McCann, author of ‘You Lost Him at Hello: From Dating to ‘I Do’ — Secrets from One of America’s Top Dating Coaches.’

This year, spend some holiday free time getting to know someone new.

What’s the best online dating site for serious relationships?

Looking for a great site for serious online dating? If your faith is important to you, Catholic Singles is a great place to start. The Catholic faith is important to us, too.

All of our efforts revolve around creating an environment that fosters our values as Catholics so you can have an environment that helps you find meaningful relationships that last a lifetime.

How much does it cost for online dating?

If your budget is tight this time of year because of holiday meals, gifts, and traveling, don’t worry! It’s free to create a Catholic Singles profile!

As a bonus, it doesn’t cost you much of your time, either. Let’s face it, setting up an online dating account isn’t the most enjoyable experiences in the world. That’s why Catholic Singles created a unique profile builder that helps you create a vast majority of your profile in less than 2 minutes. You can create your profile while you’re waiting to board that plane back home or waiting for the turkey to finish cooking.

Why should you become a member of Catholic Singles?

We make meeting other single Catholics easy and fun, and we’ve been at this since 1997.  Every month thousands of new members register and join Catholic Singles to meet other faithful Catholics. While most are here for online Catholic dating, others are here for fellowship and community. Whatever you are looking for – dating, fellowship, or just a fun group of people who share your faith – can be your home.


Ready to give holiday dating a try this year! Don’t be nervous about reaching out to others who’ve created their profiles on our online dating service. Use these fun holiday conversation starters and create an account today!