Usually when the mood strikes me is when I PLAY.  I prefer late afternoons and even more so during the evening...and my favorite is a dinner date w/ dessert (maybe even an appetizer before dinner).  

As to time of year - around holidays are NOT good...especially from Thanksgiving until mid-Feb...due to Christmas needs & expenditures taking up most of my "luxury" budget.

I had to sneak away from work in the PM (Fortuately my job gave me opportunity for this.), or after work claiming a meeting or working late.

Now that I'm single and the kids are grown up, the weekend, especially Saturday afternoon/evening is my time to hobby.

I usually hobby during the work week, even though I don't work anymore.  If I am making an appt, I will usually try for late morning, like around 11.  My local fave has a real job, so when I see her, it has to be in the evening after she gets off work.

Swim

and looks like Apr - Oct is easiest for me.  I guess that would make me a mid-year guy.

any day the coast is clear!   One really has to look at ones own life & the eb & flow of daily life to see what works.  
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Good energy, pre-meal lunch date.  The "I-am-on-a-date-want-to-be-seen-ego-stroke" fantasy is not one of mine, so evenings out don't make sense to me, unless I've actually gotten to like the woman, which is rare, since I don't like many people period.

....and always after 5:00pm - for multiple hours - in a hotel suite that I pay for. Mostly weekends - Fri/Sat/Sun - and I plan it with those I choose well in advance. The exception to this is 1 regular I'll see at her place while at home but again I like it after 5:00pm - and only when the Mrs is out of town. (Even in town I have booked a hotel room for my local choice and me on a couple of occasions - and just recently we added  a girlfriend of hers with us - and a blindfold - to a whirlpool suite - VERY HOT!) If I'm out of town, it may be any day of the week depending on my business schedule, but always in my suite, and again after 5:00PM and again for multiple hours. I like the night and the mood it sets.  I like to control the environment and go slow ....... candle lit bedroom, my music, my room service for appetizers and wine or cocktails, just a relaxed GFE/BFE for both of us! Any time of the year works for me ...... and once a month or so takes care of my need for excitement and adventure!

I prefer weekend appointments because of the time freedom they give me. I notice that more hot providers, particularly the college or grad school ones, work weekends. I will meet in the evenings after work. I have no one to report to, so there is no explaining.

Due to commitments with by business and kids, I usually plan a day and time in advance. Afternoon and early evening is best for me.

Thanks for asking!

Dear Mistress Jessica:
The question that you pose is an interesting one because you clients as well as yourself have extremely diversified lives with several responsibilities. How ever considering what your biology is and your energy level is during certain parts of the day what is usually the best time and the best days for you? Also I think a big deal for some providers is the presence of a boyfriend and when do you spend time with him as well and are you giving him enough time while still being able to persue a living.
Then there is the issue of when you would have family time if you have kids or other activities that would be near and dear to your heart. Therefore the question of time is certainly an intricate,tricky and relative question which is contingent on who you pose the question to?

alot of times Mondays because my wife won't give me any over the weekend......