Make a Holiday Dating Plan

The holidays are almost here! I love me some Thanksgiving- the food, family, thankfulness. The food. =) And don’t even get me started on how much I love Christmas. Music, Advent, Jesus, presents! So many things to love. Oh, I almost forgot Christmas trees! Decorations! Twinkle lights! Love, love, love.

Back when I was single, I enjoyed all those things, but there was also an extra amount of loneliness and sadness for me during the holiday season. Married life brings its own set of complexities to work through during the holidays (more on that another time), but generally speaking I am more content now in November and December than I was before I got married. My singleness felt heavier and harder when Thanksgiving and Christmas rolled around each year.

Part of the problem is that I was often caught off guard by my own feelings of sadness. I’d be enjoying the fun parts of the season with my friends and students, and then suddenly find myself in a lonely situation: watching a Christmas movie and wanting someone to snuggle with, realizing I was the last one at my apartment because all of my roommates had already gone out of town, driving alone to my parents’ house for holiday festivities, or not having anyone in mind when singing along to Mariah Carey’s All I Want for Christmas is You (kidding/not kidding). All of these situations created this big, loud reminder to me that I wanted to be in a relationship, but I wasn’t yet. Another year had passed, and it felt like I wasn’t any closer to my dream of getting married.

Christmas celebrates and reminds us that God came to be with us. I love celebrating that! Jesus is the savior I desperately need and knowing him is the greatest gift of my life. But even as I thanked God for sending his Son to be born in the manger, I would quietly ask in my heart, “Lord, will you send me a boyfriend, too?”

If any of that resonates with you, I’d recommend getting proactive this upcoming holiday season. I saw beautiful fruit in my life when I started seeking wisdom and setting goals in my dating life. So, it’s time to make yourself a Holiday Dating Plan. It won’t wipe out all sadness and magically make a spouse appear. But it will allow you to live with intention in the next few weeks, and I think it will help you draw close to Jesus as you take some risks with him.

Do you know that the holidays are a wonderful time to get proactive in your dating life? There are a lot of opportunities to meet new people. And remember all that sadness and loneliness I mentioned earlier? If you’re willing to really feel and process those emotions, they can be the fuel that moves you toward your desires. It won’t necessarily be easy, but I want to be the friend that reminds you that YOU CAN DO HARD THINGS.

Let’s set a few realistic goals in two categories- (1) spend time alone and (2) meet new people. Choose a couple options from each category that make sense with where you’re at right now.

Plan ahead for your alone time:

Take a look at your schedule for the next few weeks. When will you be alone? Choose to fill that alone time with some of the activities listed below that will help move you toward your desire for a relationship.

Pray– this might feel like the riskiest goal you set. You may feel like God doesn’t hear your prayers for dates and a future spouse, but he has heard every one. Keep praying! Start praying again!

Journal- Writing is a great tool to use in order to process your feelings in a healthy way, rather than being surprised or overwhelmed by them. Here are a few questions to get you thinking and writing:

  • How are you doing? How do you feel about your work, home life, dating life, family, friends?
  • Did you start 2016 with any dreams for the year? Did any come to fruition? Did any of them not come to pass? Have you allowed yourself to grieve the loss of that dream?
  • How do you feel about the holidays?
  • When have you felt lonely recently? How did you work through that? God often uses loneliness to remind us that we need time with him, time by ourself, or time with others. Which of those areas could you work on?
  • What do you think and feel about the idea of being proactive with your dating life? Excited? Irritated? Overwhelmed? Why?
  • How do you feel about taking some risks in order to meet new people?

Read– The older I get, the more I realize how important it is to read my Bible. It’s where it’s at, people. What will you be reading in the next few weeks? I’m enjoying Tim and Kathy Keller’s Psalms devotional and I’m hoping to use the She Reads Truth Advent plan this year. Spending time with God by reading his Word will hopefully help you preach the Gospel to your own soul. Your greatest need has been met in Jesus. He knows all the other things your heart desires, and he’s able to give you the strength and wisdom to move towards them. Now may also be a good time to read a dating or relationship book. I listed a few that I recommend in a previous post, including my favorite dating book and my favorite marriage book. And a friend recently told me to check out this one.

Plan to meet some new people

If you want to end up in a serious dating relationship with a great guy, the first thing you have to do is… meet him! How many new men are you going to try to meet by the end of the year? I think 5 is a great goal, but pick any number you want.

How are you going to meet these new men? There are three options:

Meet someone through a mutual friend- You’ll probably see a lot of your friends and family in the coming weeks. Do they all know you’re interested in getting set up on blind dates? Here’s the risky part- you’ve got to tell them directly. When your aunt or cousin or that random friend you see once a year sees you at a Christmas party and asks, “How are you doing? What’s new in your life?” be ready with an answer like, “I’m doing well! My job has been stressful over the last few weeks, but our big project is almost complete. I’m planning a trip to [insert fun destination where you’re headed next summer because you’re rocking the single life and you’re fabulous like that] that I’m really looking forward to. Oh, and I’ve been trying to get more proactive in my dating life. Let me know if you know any great guys I can meet.”

Does that sound a little awkward? Well, sure. Especially the first time you say it. But if you see each interaction as practice, you’ll get better at it. Some people you talk to won’t quite know how to respond, and that’s fine. Just ask them how they’re doing and move on. Other people will LOVE that you mentioned it and will want to hear all about your process. And you might end up meeting some great men. Woo hoo!

Meet someone by being in the same place at the same time and introduce yourself- I know it can feel like you know all the people and there just aren’t any new options out there. But that’s not true! There are many new people right in the area where you live. It’s time to go meet them! Plan some outfits you feel confident in so you’ve got options for various events you head to this month. Make eye contact, smile a lot, and pay attention to the person you’re talking to. You can do it! Choose some of these ways to meet new people:

  • Sit in a new spot at church.
  • Go to an event at church that you haven’t attended before.
  • Go to a different service time at your church.
  • Check out a different church’s Christmas events with a friend.
  • Go to the grocery store right after work or in the evening. Not joking. This is when single men shop.
  • Go to a Christmas party.
  • Throw a Christmas party and tell your friends to invite their friends and friends of their friends.
  • Find new ways to serve others during the holidays- at a Thanksgiving meal for the homeless, at Food Bank, a toy drive, etc.
  • Update your online dating profiles and plan out more time for online dating.

Meet someone through a new friend- Many of the places or events I listed also provide opportunities to meet new people of all ages and stages, not just eligible men. So, by stepping out of your normal routine, you will be able to form new connections and friendships. What a gift! Especially during a season that can feel more lonely. If you get used to casually mentioning your dating life as you get to know people (see above), you’ll open up the possibility of meeting men they know. For example, let’s say you decide to sit on the other side of the sanctuary at church next Sunday instead of in your usual spot. During the meet and greet time you turn around hoping to find a cute guy with a good job to say good morning to. Instead, you shake hands with a sweet, chatty woman in her sixties named Gwen. Womp, womp. Except, wait. How fun would it be to be friends with a spunky woman named Gwen? I like her already. Say hi and give her a hug next week when you see her. Answer all the sweet questions she asks you and ask her about her life, too. Soon you might find out that her son, or grandson, or neighbor, or dentist is in his twenties/thirties/whatever-age-you’re-looking-for and she’d love to introduce you to him! Isn’t Gwen the best? A new friend and possible blind dates. Win, win.


Think through your Holiday Dating Plan. Write it down. Share it with a couple trusted friends who will pray with you and help you process things that happen. I know that setting dating goals and getting out there to meet new people can be risky and overwhelming. Look for the fun parts and keep praying! The Lord will say yes or he will say no to your requests, but his answers are always for your good and his glory. I’m cheering for you as you take steps toward your desire for marriage. Happy Holidays and Happy Dating!

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