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HOLIDATING: Dating during the Holidays


Kait & JJ Tomlin

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Today we’re talking about dating during the holidays, the do’s, the don’ts, where to meet people, creative date ideas, and more! 


Hey guysss! Welcome back to our mini season about being Single During the Holidays…we’re getting into the fun stuff today talking about DATING during the holidays aka holidating!! 

Cuffing Season

When Kait looked up the definition of cuffing season she found out, is the cold autumn and winter months seen as a period when it is especially desirable to enter into a romantic relationship. JJ added that it’s cuffing brought on by the cold and desire to cuddle out of loneliness. So wowza we have LOTS going on when it comes to cuffing season, y’all. 


We’re talking about holidating today! To clarify, we are talking about the DATING STAGE, not relationship. For clarity this is our definition of dating, a time when you go on dates and build FRIENDSHIP with another man or woman of God who is of interest to you. On each date in the dating phase, the goal is to take it ONE date at a time as you approach the other person with curiosity. The point of the dating phase is ultimately to see (through TIME) if you want to be in a RELATIONSHIP with the person you are building friendship and going on dates with. 

So this episode is more about MEETING people and going on those first few dates with them, NOT how to navigate the holidays with your boyfriend or girlfriend (we have another episode for that). 

We have an AMAZING resource to help with this! It’s called, “How to Show Interest.” You can download it for FREE by going to 

Where to Meet People During the Holidays

There are SO many opportunities to meet people during the holidays, even if you’re an introvert! 

Accept as many party invitations as possible to all the holiday parties IF you’re wanting to meet people and date!! How do you get yourself invited? Tell people you want to go to events! If you know a friend is going to a party (and it’s not like a birthday party) ask them if they mind if you go too. This is BOLD, but remember that you’re trying to put yourself out there. 

A note on wingman and wingwoman: I wouldn’t go with a group of 5 people. Go with ONE or TWO other people. It’s overwhelming and intimidating for a guy to walk up to a group of 5 women talking. If a guy wants to ask a girl out, he’s more than likely not going to walk up to a group of 5 women to do it. For guys, it’s a little different because you’re going to be the one going to the woman to ask her out. 

Go to holiday events! Not just parties, but events like a tree lighting ceremony or a baking class. 

Volunteering! At church but also outside of church. What better place to meet someone then if they’re serving?! 

Church Events! Lots of churches have these, PLUS there is no reason why you can’t go to these events even if they’re not at the church you go to regularly. There are worship nights, holiday socials, ALL KINDS OF THINGS! It’s also a wonderful idea to SERVE at these events. 

Setups! This can’t be from just anyone. This has to be from someone you TRUST who they know, someone who may have interest in you. The thing with setups is, don’t just ask for them, FOLLOW UP! 

Dating apps!!!!! This is the number one way, truly, there is a spike in people using dating apps during this holiday season. If you’ve felt burnt out with dating apps the first thing you need to do is renew your mind when it comes to dating apps. We teach extensively about this in the School of Dating, but online dating is all about MINDSET. 

We love the dating app, SALT. This is a Christian dating app, which is amazing and takes some of that guess work out. You can use code HEART for 2 weeks of premium for FREE right now! 


You don’t have to feel all the pressure to date during the Holidays if you are in a closed season of singleness and don’t want to be dating. There’s so much pressure and it IS a good time to meet new people AND at the same time, you don’t have to feel pressure to date date date because everyone else is right now. 

Do's and Don'ts of Holidating

DO everything we just talked about above! 

DON’T jump the gun and bring your NEW person to holiday parties/work parties unless you are in a committed relationship because it’s TOO much PRESSURE. Boundaries and pace!

DON’T buy gifts! Do you buy gifts for someone you are newly dating? No. Don’t buy them anything BIG if you do get them something. If it’s super new, we don’t suggest getting them a gift at all. Wait until you’re in a serious committed relationship. You CAN get them LITTLE things that are more, “I saw this and thought of you,” and LESS “this is a Christmas gift for you.” 

DON’T bring them to FAMILY outings/family Christmas or Thanksgiving dinners! You just met them, absolutely NOT unless you’re in a committed relationship. BECAUSE this adds SO much pressure. You want to make your own assessment before bringing family into it. 

DON’T rush the process! This time of year is VERY romanticized. It’s easy to get lost in the feels and all the sentiment of doing Christmas-y things. Don’t throw your good wisdom and timelines out the window because you’re feeling extra feelings. Don’t rush the process. One date at a time. 

Creative Holidate Ideas

  • Ice Skating
  • Go to a drug store (CVS) - Buy your favorite Christmas item that reminds you of childhood, your favorite christmas snack, a christmas accessory that they have to wear the rest of the night
  • Cookie Decorating
  • Volunteer Together
  • Christmas light tour - Hot Cocoa and driving through a neighborhood to see lights with a christmas playlist playing…. BONUS pizza in the car after.
  • Indoor Christmas Picnic by the fireplace or Christmas tree - put up a christmas class on the TV in the background
  • Gingerbread house competition
  • Christmas Karaoke
  • Make handmade Christmas Cards or handmade ornaments 

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Kait Tomlin

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Kait Tomlin is a best-selling author, speaker, popular relationship coach, and the founder of Heart of Dating. She helps thousands of men and women on their journeys through the conversations on the Heart of Dating Podcast, which launched in 2018.

Through her ministry, Kait’s mission is to empower both men and women to have the courage to own their story, walk in victory, thrive with purpose, and discover clarity and vision in their life and relationships. In her new book, Thank You for Rejecting Me: Transform Pain into Purpose and Learn to Fight for Yourself, Kait vulnerably shares how she grew through her deepest, darkest rejections and offers readers the tools to heal from the past, take back their power, and walk in strength, victory, and love into their future. Kait currently lives in the Los Angeles area with her husband JJ and their pups Lovey and Teddy. She loves sunshine, walks, Jesus, and lip syncing to Celine Dion.

JJ Tomlin

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JJ Tomlin is a missionary kid born in Belgium, originally from Tennessee, and currently residing in the OC. He currently works in Gaming/E-Commerce, enjoys watching his Tennessee Titans on Sundays with his Goldendoodle Teddy and loves working with Christian men to raise the bar in singleness and dating.

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