Where a POT takes you for your date says a lot...
Just my two cents. Everyone has different experiences but in all my years this is what I have noticed.
It isn’t necessarily about how much a date costs a POT, but more about where he takes you and what time of day/week that may be.
Sometimes schedules dictate the time of day/week, but more often than not a POT will take you someplace based on how they see the future relationship unfolding.
My general rule of thumb is:
Weekend verus Weekday
Weekend dates are the best. I don’t mind missing out on other activities if it means I have a promising POT date. Especially since most of my weekend activities tend to go all night anyway so I can always show up to said event after my date. An older gentleman is usually willing to go on weekend dates with someone he is very serious about getting to know. He is likely more serious about the whole SD/SB thing in general. He doesn’t mind canceling or rearranging his plans to accommodate you. Or, if he doesn’t really have any plans and is kind of a lone wolf, he is more likely to become attached to you so he finally has someone to hang out with on weekends. Expect weekend getaways to fun locations, if you start an arrangement.
Weekday dates are usually easier and less work. He is likely meeting up with you right after work but before going home to the wife and kids (if he is married, obviously). These dates tend to start a little earlier in the evening and will be more cut and dry. He will likely bring up the details of the arrangement earlier in the date to get that part out of the way and see how much time he should invest. On weekdays, time is money. He has to go to work in the morning and doesn’t want to be out all night for no reason. Weekday dates are the best way to land a married SD (my favorite kind). His weekends are usually dedicated to his family and therefore you won’t be going on many getaways with him but may accompany him on business trips.
Day versus Night
Evening/Dinner dates usually mean the guy is very serious. He might be Splenda but he will be very serious about his Splendaness.
Day/Lunch dates usually mean the guy is not sure about the whole SD/SB thing and doesn’t want to disrupt his other evening plans just for you.
Trendy, Upscale Bougie Cocktail Lounge and Eatery
He wants to show you off and see how you do in such an environment. Depending on which city you live in, he may be testing the waters to see if you can handle yourself around celebrities, powerful business men and others who are in an “older man, younger woman” relationship. You will likely see other SBs at these types of places and you will definitely see celebrities if you live in NYC, Chicago, LA or similar locations. Dress is usually similar to going to a club but perhaps with a slightly longer hemline.
If you can handle yourself appropriately (according to him) and other men check you out in this sea of beautiful people, you are IN. This guy will likely be a very good SD assuming this isn’t a ploy and he isn’t pure salt. Expect nice hotels, fabulous restaurants, shopping sprees and surprise gifts on top of a hefty allowance. He wants a fun girl and will provide luxury experiences as long as you keep it fun. Let loose around this type. He wants you to be the center of attention in any crowd without forgetting that he is the one you are going home with.
Upscale, Classy, Expensive Restaurant
He is taking you here because he wants to impress you. This type of setting isn’t so much about seeing how you act in public but more about how you carry yourself as a person in general. Please, thank you, napkin on your lap, using the correct fork, ordering the appropriate wine for your meal, etc. are all things he will notice. Doing something wrong may not be a deal breaker but it may make him lower his offer without you even realizing it. Dress is usually more conservative and less colorful. A figure hugging dress that hits just above the knee with some modest (3-4 inch) heels. You can show a tad of cleavage but don’t over-do it. A guy who chooses this type of restaurant is looking for someone who won’t embarrass him or draw much attention while in public.
He will likely be a stable SD (again, assuming he isn’t pure salt) and will offer a modest allowance and will treat you with the utmost respect at all times. This type of SD tends to be the most work, in my experience. You have to be “on” more often than not with this type.
The only exception to this rule with this type of location is if it is a day date. Day dates at restaurants that are usually only busy after 8 p.m. is a sign that he wants to avoid crowds all together. He may be embarrassed by the idea of you two together OR he may frequent that restaurant so often that it no longer feels special to him so he doesn’t mind going there during the day.
Casual, moderately priced, semi-trendy restaurant
A guy who takes you to a simple, no-frills type of restaurant is likely looking for the same thing in his SB. He wants you to be casual, easy-going, and fun without being wild. Smiley, girl next door types will do well with this type of SD because you are basically exactly what he is looking for without even trying. Dress for this type of restaurant is casual cool. You can get away with jeans and a trendy top and heels. If you wear a dress, a sundress or girlish dress are good options. Your makeup and hair should still be on point regardless of outfit choice. You can drink a little more at this type of restaurant because chances are it has a casual and fun vibe. These types of places are usually loud with other people’s conversations.
This type of SD is good for a moderate allowance, gifts, trips and fun adventures. He may not buy you Louboutin every month but he will buy you smaller gifts if you simply ask. You will likely stay in business class all the time, including hotels. This isn’t a bad thing at all. You will still be comfortable and it’s still better than making your own bed or flying coach.
Cafe or Diner
These places are usually reserved for day dates. Guys that choose this type of place are usually salt or Splenda, in my experience. They are looking for more of a girlfriend than anything and don’t see the point in “pulling out all the stops”. These are the guys that tend to say they don’t want it to feel like an arrangement. If you choose to pursue a guy who chooses this type of place, be prepared to divulge your entire life story in detail. Since it is during the day, without the sexiness and allure of the night, it encourages the conversation to become very familiar, quickly. Dress for this type of restaurant is simple. Jeans, cute sandals and a low cut or v-neck shirt are appropriate and really all he deserves given the location.
These types of guys can turn out to be good for a decent pay-per-meet arrangement but they likely won’t be very reliable and may never really spoil you.
And this is why I always try to get the guy to choose a restaurant and day of the week. Even if I have to suggest a place or day, I give two or three very different options and then let him pick from those. What he picks says a lot.
Also, please note: These all are based on an actual planned first or second date. Where you meet a POT while freestyling doesn’t really factor into this at all. If you meet a guy at Starbucks and he then takes you to an upscale, bougie lounge… you are winning.