top of page


Tis the season…so as an online dating coach and consultant, I’m sharing frequent questions I get this time of year from singles, from friends …from the media. (See recent BBC newscast)

  1. 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 first as the Founder of Its Just Lunch and now the Founder of 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!

2. 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 just 1-2 dates—-you can show off that new sparkly dress and heels or dig out your Christmas tie. 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!

3. I just met someone I like—-just one date so far. How many more dates til I invite her to my firm’s holiday party?

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

Extended through Today!

4. When do you subject them to your family?

Ohhh, the word subject here makes me nervous. Is it generally a happy time with your family or a dysfunctional once a year get together? Also, it depends on logistics. If it’s generally 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.

5. I’ve had 3 dates with a guy I really like. How many dates til I buy him a gift?

Ahhha---see this photo I made just for you

6. I just met someone last week and we’ve had 2 dates. Is it too early to ask her to a New Year’s Eve party? It’s a big black-tie affair in Chicago where tickets go fast, and my friends and I are getting a table. What do you think?

Yes. Why not? I believe in keeping the dating momentum going---two dates in one week means you enjoy each other’s company. Ask her in person on your next date. People plan New Year’s well in advance so don’t be shy.

6. I’m a divorced guy in my 50’s. Most women I date are similar ages, and we all have kids, some grown, but sometimes teenagers or younger. If I’ve been dating a woman for a few months, I expect to buy her a Chrisymas present. But should I also purchase something (albeit small) for her kids? I’m not their stepfather and I don’t want to overstep my relationship, but I want to be polite.

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

7. I’ve been dating a guy for 4 months and we are approaching the holidays. Even though he has been divorced over 5 years, he still spends Christmas Eve, Christmas Day, New Years, etc. with his ex-wife and their kids as if they are still a family. I don’t have kids, and I certainly don’t want to spend the holidays with my ex-husband. Should I be jealous? Or at least a bit miffed that my boyfriend is spending all Holidays with his ex-wife and kids and very little time with me? Should I say something?

You’ve been dating 4 months, not 4 years. This is your first holiday season with this new man---I recommend picking another day (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, friends. And don’t forget Cyber Week 20% off ends today! It’s not too late ever to date.

Recent Posts

See All
bottom of page