If you've been reading my posts here for a while, you know that I generally advocate against scheduling sugar dates on major holidays. I often suggest casually mentioning to your SB a few weeks in advance that you will be "out of town," "hosting family or a friend from out of town," or whatever works to make it clear that she's on her own for Xmas dinner, NYE's celebrations, or a huge Valentine's Day romantic (and ridiculously expensive) dinner.
For those SD's who have an SO, the reasons are obvious as you will presumably be with your SO and others on these key dates. But even if you are sans wife/GF or even a civilian FWB, sugar dates on these occasions are typically more expensive with potentially less (or at least no incremental) BCD time. Add to that the potential for an SB to read into such a date more than you intend (like maybe you want to escalate this relationship/dump your wife or SO, or something else) and it's generally better to have her "miss you" and then be happy for your post-holiday catch up date and all that entails.
Well, I have been doing none of that with my current #1 SB. In fact, I've been doubling down on upscale holiday dates. For transparency, I do not have a wife/GF or civilian fuck buddy opportunities (well no opportunities I want) in my life. So I'm free to break my own rules without fear of needing to hire an attorney or go to the Emergency Room to remove a pair of high heels forcibly placed inside my body (this time without lube! LOL).
I did attend a friends & family Xmas dinner this year, but I bought her several Xmas presents (5 gifts, total budget was less than $300). But I skipped my social group's annual NYE party and took my SB to an upscale and rather pricy NYE dinner, dressed in formal attire. I have also made plans for Valentine's Day including dinner at Mastro's in Malibu with a view of the ocean, roses delivered to her (at my place - her mother who "does not allow her to date yet" - would ask too many q's), and an overnight in a 4-star hotel.
Why?
Because she is 20 and appreciates it. She's never had this glimpse of an upscale lifestyle before and she's - so far - soaking it all in and showing me how much she appreciates Daddy for treating her like a Princess. And, of course, I'm just soaking up the dirty looks I get from disapproving women and jealous men I see at these places when I stroll in with a 20-year-old sexy Asian spinner on my arm.
So maybe I need to rethink my rules around this? Or maybe I just need to refine them a bit. I would not do this with an SB who was always pushing for more time, more money, or who did not demonstrate considerable appreciation for my generosity.
What about you? Do you schedule sugar dates on major holidays? If you have an SO or other social obligations on major holidays, do you schedule an alternate date (I think Feb 13 is called Mistress Day!)?
Or are you always "out of town" and then keep your regular sugar schedule like the holidays do not exist?
Life is good
The Cat
My primary SB and I have been together for more than seven (!) years and the holidays can be a problem. The one for which we always plan to be together is Valentine's Day. Other than that, it varies from year to year with other significant others and both our families playing a role. This year, I spent Christmas and New Year's out of the country and will be back with my primary SB tomorrow. This does not negate the fact that I'm havng dinner with a POT tonight! Sometimes I have several plates spinning... so far I've managed to survive... but sometimes it ain't easy. Pray for me! 
I have had positive experiences with major holidays with younger SBs. They really do appreciate the attention and finer experiences. It factors into their calculus, even if it is subconscious.
However with older SBs I stay far far away from holiday dates. The relationship escalator with them is real.
since I am happily married and all my SBs know this, they don't expect me to be available during major holidays. And this past holiday season 2 out of 3 of them were out of town visiting family so it was a moot point anyway. However the 3rd one, who is actually my favorite, was in town and I did not want her to be alone on Christmas. I invited her to join me and my wife and some dear friends (who know about my sugaring) at our home for Christmas. But she wound up making plans to be with friends. So I got points for offering.
I avoid such dinners because, basically I get bored. My serious question to my fellow diners is: what do you talk about? It gets worse if you tell them no phones during dinner because that makes them nervous - what if she's missing a super important text from her BFF. Then what? Sure one can comment about the wine and the Chilean Bass, but then what?
and then we discuss the first thing that pops up.
Ba-doom.
But seriously ladies and germs...
I often dine out with the gals I see, often at my home. And what we talk about varies with the gal. Sometimes it's about our families, or I talk about my work, or we discuss world and national events, or movies, or music, or books we recently read, or science. I"m sure I'm leaving a lot out.
The point I am making is, I select the regulars I see based as much (and lately even more) on how I get along with them rather than purely carnal considerations. In the long run, this makes for more satisfying relationships and fonder memories. To put it another way, when you truly care about a person, then you can read the phone book. (It was a thing, ask your parents.) and it still involves you. It's the listening more than anything.
There is a down side: A long time favorite (under the radar gal) suddenly passed away. To live long is to mourn more.
