Not a new discussion, but I thought it would be timely to discuss once more.  

 
What are you doing about Valentine's Day with your SB (or SB's)?  Are you scheduling V-Day dates?  

 
If you are, what date, or dates (before, on the 14th, or after)?  Are scheduling romantic and/or expensive dinners? Are you buying/sending flowers or other gifts? Are you considering this as one of your scheduled dates? Are you taking her somewhere local, or out of your area?  

 
If you are not, why? Are you busy with an S/O? Is she busy with an S/O? Are you worried it will send the wrong message (i.e.: catching feelings?) or are you worried about creating a bad "holiday date" precedent?  Dis you proactively preempt any discussion of a V-date by telling her you will be unavailable (out of town, working, budget issue, S/O, discretion, ect.)?  

 
How much of your decision is based on issues like OpSec or keeping your Sugar life UTR?  

 
For me this year, I am not booking anything on the 14th, mostly because many of my SB's have SO's (some have BF's,  one has a Hubs, and some have GF's).  But I am scheduling V-Dates on other days with 3 SB's. And I did buy small (less than $50) presents for all three of them.  

 
I don't believe there are any hard rules on this. I think each of us needs to consider what makes the most sense for each SB.    

 
Life is good

 
The Cat

My main and I have a date set for Sunday.  She's working Friday and Saturday so crashing hard.  We have an early morning.  She's surprised me with an event in dtla.  She's super excited for it.  I bought her some gifts and have flowers coming to her door on Friday.  I'm planning lunch and the afternoon with her.

Friday I actually have a first date with a pot.  We talked for a while, fell off, she reached back out.  Will report on this next week when I fill in all the reach out from the past and how they all went.

Saturday night, I'm seeing an old SB that reached out.  Late afternoon to early evening.  She gets up super early for work.  We met for lunch and she told me how much she missed me.  She's a 10 in looks so I'm not complaining she's back.  This will be dinner and BCD.

Normally, I lay low unless it's someone I've been seeing a while.  Last year was my first VD with my main and I making a serious run at it.  I was seeing one other girl then but she was out of town.  

My SBs know I'm happily married and my awesome wife knows I love my SBs. Last week I had a regularly scheduled date with SB #1 and gave her a Valentine's Card, and a small gift and some chocolates. She loved it!  On Valentine's Day I'm taking my wife to a romantic Hacienda in the mountains where we will enjoy dancing and food and stay overnight.  And the next day I'll be visiting SB #2 and will present her with the same card/gift/chocolate.  I also have many old SBs I'm not seeing anymore but stay in touch with.  3 of them actually have birthdays on Valentine's day!  So I'll be sending out quite a few Happy Valentine's Day texts, thinking of you with love, etc.

My plan for Valentine's Day this year is to reconnect with my ex K-girlfriend. A beautiful 8 year relationship that ended last year when I started thinking the grass is greener on the other side and dipped my feet back into the sugar bowl.  

I don't know how I'm going to do it, considering she lives on the opposite coast and hasn't answered my calls or texts since the day after Valentine's last year.

I legitimately will be out of town at a family gathering.  Even if I wasn’t, my main SB would not be satisfied with anything less than a very expensive purse or other gift, so I’m not planning to even text her that day.  Another long time SB is married, so that isn’t an issue. In any event, I am reluctant to even text the rest in my rotation because, as you mentioned, it may be misinterpreted as feelings which will only create headaches for me.  

I suggested to my SB dinner and some light S&M sex...light bondage etc for Valentines and she said yes.  I was in part kidding.  Score...she is getting better everyday.

Bought some Venus et Fleur and chocolate for her.

of valentine's day is too hokey for me..

For the last time. Gotta get one last shot at that great piece of ass.  But her services are no longer in line with her expectations.  She seems unaware that I've told her....

It is def hokey, for sure.  But it's also an opportunity.  I send Happy Valentine's Day texts to many SBs I have not seen in a while, just to let  them know I still think of them with affection and that they are welcome to reach out if they want.  It's an easy way to kindle/rekindle an arrangement that does not come off as desperate or needy, since you have the "excuse" of Valentine's Day.  And I def send an affectionate message to all of my current SBs, (in addition to some small gifts), and always get an equally affectionate message in return.  It's easy enough to do, and if the girls expect it, you run the risk of disappointing them if you don't.  I know it's just a scam to sell greeting cards, candy and flowers.  But it's also low key enough that a few small gestures go a long way.  Don't even get me started talking about the expectations around Christmas!

-- Modified on 2/13/2025 1:33:22 PM

I second that, Sweetman! It is indeed an opportunity to send affectionate texts with a wrapped heart emoji or some similar graphic to let your current stable of fillies know you are thinking about them, but also as you point out it's a great way to get back in touch with those who have fallen off the radar as a 'tickler' to remind them you are still alive and kickin' and available for some lovin'.  

Exactly!  When you look at it this way it's almost as if Valentines Day was invented for Sugar Daddies!  It give us a chance to say something sweet and loving, without them thinking we're getting too emotional or "catching feelings".  A card that says "I love you" any other day of the year could be construed as creepy.  But on Valentines Day it's just a Valentines Day card!  And hopefully gives the impression that we care about them more than as just a great fuck!

Amazing bareback sex but I had to finish w a condom unfortunately (she isn’t taking birth control anymore)  

I got her a bouquet of flowers for v day and a dress as a gift — on top of ppm this cost me like 170 bucks total on clearance — but made this encounter amazing

she was treating me like a king  - and moaned and scratched like no other time. I was so exhausted after one round but then she started blowing me and made me hard for a second time and I came in her mouth.  

This is precisely why I will never ever go back to escorts — the simulation of reality just isn’t same as reality . I realize maybe this is simulation too but as close to real as can be  

I  do have a couple of backups — but I just sent them a message, sent one flowers . They are more distant and also more transactional. Not meeting anyone today

-- Modified on 2/14/2025 10:10:39 AM

Saw my main today.  We had a picnic in the park.  I bought her a few gifts and had flowers delivered to her home on Friday.

She had me close my eyes while she brought my gifts out.  It took her two trips from her car.  I open my eyes and she has baskets of gifts.  She bought me books from series I had wanted to read.  Some magazines she thought I would love.  And a bunch of candy.  Flowers.    Fuzz socks and slippers.  A blanket for us to cuddle under together.