🎄 10 CHEEKY HOLIDAY DATING TIPS
- andrea6822

- 2 days ago
- 3 min read

(That Actually Work — Even After Eggnog)
Holiday stress reveals everything
If they lose it over traffic, airport delays, or parking at the mall, imagine them during a real relationship problem. December is a free personality audit.
Don’t confuse holiday loneliness with chemistry
Candles, cold weather, wine, and twinkle lights create false positives. Attraction should still make sense in January.
Keep first dates “holiday-light”
Hot chocolate, coffee, or a walk with decorations beats a high-pressure dinner. Chemistry hates expectations.
Ask one unexpected holiday question
Skip “What are you doing for the holidays?”
Try: I’d say it more like “Oh my gosh, you know what my family does Christmas Eve that is totally funny to me?....(you answer) Then say “Any goofy traditions in your family”
(For me, Andrea, it just sounds like less of an “executive recruiter” type question and more how I’d say it on the date…just saying!”.)
The answer tells you everything.
OK, there’s 6 more below this line. But just wanted to go over my Holiday Hours!A. Don’t use my calendar (I closed it for a few weeks)and if you want to do a 15-minute call with me---Text me directly at 760-898-1727 (I’m on the East Coast) and I’ll pop you in for new people.B. My current clients—most of you are set for January with me. If not, email me.C. I have limited openings on Monday, December 22---again, text me.
D. I can take a few new callers on December 29 and 30. But let me know ASAP please as it’s jumping into the busiest dating time of the year.
E. Week of January 4 (hey, that Sunday is the busiest online dating sign up day---it’s called the Super Bowl of Dating) I’m back to my normal business hours.
Oh, one more thing: Two old good friends who run Match.com and Bumble told me starting December 27-January 6 they expect between a 24-43% jump in paid sign-ups ---yay, for us!!!__________________________________________________________
Watch how they treat service staff in December
Servers, drivers, baristas. Generosity under stress is a major green flag.
Snappy behavior earns instant coal.
Flirt with cozy confidence, not over-the-top seduction
Holiday flirting should feel warm, playful, and nostalgic—not try-hard or thirsty. Think fireside charm, not nightclub energy.
No trauma-bonding over family
A funny story? Great.
A 20-minute therapy session about Aunt Linda? Hard no. Save it for February.
If they disappear between Dec 20–Jan 2, believe the data
They’re not “busy.” They’re selective. Healthy daters communicate—even briefly.
Gifts should fit in a stocking, not a safety-deposit box
Thoughtful = charming.
Expensive = pressure.
Jewelry before exclusivity = accidental engagement vibes.
You’re not casting a spouse during the holidays
You’re gathering information cheerfully. The real test is whether you want a second date in January—when the lights come down.
Happy holidays to all my clients whom I love working with so much…and to those of you I have not met yet! Enjoy your friends and families.
Much love,
Andrea(My homemade gifts are done that are being sent to family far and wide---My Grandma’s LadyLocks, Fudge and a few other goodies---had to share a photo!)
And one more idea….
My two favorite gifts I’m giving this year beside fudge and LadyLocks:
1. My Book: 2nd Acts: Winning Strategies for Dating over 50
2. Arthur Brooks: The Happiness FilesI
f you don’t know him, geez, I talk about him all the time and am a big fan. No psychobabble. Who is he? A guy who started teaching at Harvard Business School a few years ago on “Leadership and Happiness”. Everyone thought this was a weird class and hardly anyone signed up. Now he has a crazy wait list for his class and when I work out I listen to his podcasts—Truly, he is for every age. I just LOVE him!




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