Frequently Asked Holiday Dating Questions


Tis the season… so as an online dating coach and consultant, I’m sharing frequent questions I get this time of year from singles…  

Is December a Good Month to Date or Should I Wait?

Ohhhhh, go for it! There is not a bad month of the year to begin dating – truly! With over 25 years of dating experience (as the founder of Its Just Lunch and Thirty-Three Thousand dates), I love December. It’s festive. Holiday parties. Good cheer. Good moods. Lighting of Christmas Trees. Hanukkah. Christmas cookies. Mistletoe. Oh wait, this is probably the happiest month of the year to date!

My Friends Told Me to Wait Until January to Try Out Online Dating. Thoughts?

Nope. When YOU are ready, you are ready. Many of my clients get invited to holiday parties after the first two dates – why not show off that new sparkly dress? There also seems to be a plethora of Ugly Christmas sweater parties this year – why wait? You can still date in January but think of the potential fun Christmas friend and work parties with a date you may have missed out on!

I Just Met Someone I Like – Just One Date so Far. How Many More Dates Till I Invite Him to a Holiday Party?

Well, since we are under a time crunch, normal rules don’t apply. Assuming that you have a second date planned this week, that’s the time to ask him! No need to be shy – it’s a likely yes, as who doesn’t like holiday parties, especially since last year we had none?

When Do You Subject Them to Your Family?

The word subject here makes me nervous. Is it generally a happy time with your family, or is it a dysfunctional once-a-year get-together? Also, it depends on logistics. If it’s a fun family holiday, and they live in the same geo area (one that doesn’t require flights, hotels, etc.), why not? Then again, if you are miserable during this family day, don’t share your misery.

I’ve Had 3 Dates with a Guy I Really Like. How Many Dates Till I Buy Him a Gift?

Let me use a graphic instead of long explanations.

Should I Purchase Gifts (Albeit Small) for the Kids/Grandkids of a Man I’ve Dated for a Few Months?

This is a thoughtful question. If the kids are in their 20’s, no. If you’ve never met the kids, no. Why confuse them? Now, if the kids are in the 12-17,18-year-old range, a small gift is a sweet idea. A $25 Starbucks card would be appropriated.

If the kids are very young, no. If you are partaking in their holiday festivities, a box of chocolates or gingerbread cookies will go over well with the little ones.

Should I Be Jealous (Or Annoyed) If My Boyfriend of 4 Months Prefers to Spend the Holidays with His Ex-Wife and Their Kids?

You’ve been dating 4 months, not 4 years. This is your first holiday season with this new man – I recommend picking another day (say, December 26) to celebrate together. Jealous? That will get you absolutely nowhere in a relationship, alienate him and kudos to him for an amicable relationship that he must have with his ex… and he cares about his kids!

Keep the questions coming, ladies. It’s not too late ever to date.

Have you wondered about any of the above questions? What answers have you received to date? Do you have a question (or more) of your own?

Let\’s Have a Conversation!


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