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Arranging Your Sugar Baby First Date

From, image by Kristin-and-Adam

From, image by Kristin-and-Adam

As a follow up to my popular article C.J. Asher’s Guide To The Sugar Baby Arrangement, I’ve decided to do some follow-up articles related to the “sugar baby” and “arrangement” lifestyles which I’ve indulged in myself over the past several years and have gained some fun and amazing experiences from.

First up on our agenda, planning out the first date with a sugar baby. While this article is primarily written for the sugar daddy or sugar mommy who will be planning out and paying for the date (chivalry isn’t dead, people!), sugar babies can also learn a few tips and suggestions for what you should (and should not) expect from your first meeting with a potential benefactor.

Don’t Rush into the First Date
Okay, so you’ve met the perfect sugar baby, most likely through a website such as or… they’re stunningly attractive, have a great personality and you share some common interests and hobbies. You want to meet them as soon as possible, but before you do, remember that an arrangement isn’t a sprint, it’s a marathon. Even with a short-term arrangement, a sugar daddy or sugar mommy shouldn’t expect a date after the first e-mail, shouldn’t try to cram in as many dates as they can as quickly as possible or expect to be in an arrangement before even meeting in person. Get to know your sugar baby before meeting face-to-face: ask some basic questions about what type of arrangement they’re looking for (you can discuss details such as how generous you can be and what you expect in terms of availability from your sugar baby on the date), what they like to do for fun, their past experiences with arrangements and what types of restaurants they enjoy. Even though you’ll be generously compensating your sugar baby for their time and companionship in the long run, make sure your sugar baby will be going out on a date that they will enjoy as well and won’t be bored or subjected to an activity or experience that they won’t enjoy simply because it’s what YOU want to do. In other words, your sea-sick date won’t jump on the opportunity to hang out with you again if your only idea of a fun time is going out on a fishing boat for the day!

Don’t forget to K.I.S.S. (Keep it simple, stupid!)
Okay, wealthy sugar daddy or sugar mommy, so you want to take your potential sugar baby out and show them the time of their lives: chauffeured limousine rides, a dozen red roses, the most expensive restaurant in town followed up by blowing thousands of dollars at a nightclub and casino. Slow down there, Casanova! Never go overboard with your plans for a first date with a sugar baby. The first date should be an opportunity to get to know your sugar baby, discuss the arrangement and see if there’s chemistry. Also, nobody wants to either spend thousands of dollars or be stuck with someone for multiple hours if one or both realizes, within the first few minutes of meeting, that they aren’t interested in the other person.

Be Romantic and Classy
Despite not wanting to go overboard, you can and should try to plan a romantic time to impress your date and show them that you’re committed to a true arrangement. If your sugar baby desires, plan out a romantic evening at an upscale restaurant and perhaps a fun activity together after such as drinks or a comedy show. Show your sugar baby a lifestyle that she may not be accustomed to and that you’re willing to spend a few dollars to impress them… as they say in show business, always leave them wanting more!

Don’t Do Allowances or Gifts on the First Date
While this may seem counterintuitive to what an arrangement is all about, unless you’re on a website such as, I don’t recommend providing a sugar baby either a gift or start an allowance on the first date. While a sugar baby’s time is valuable (as is everyone’s time), you shouldn’t commit to splurge with a financial commitment or gifts on the first date. Much as there are sugar daddies and mommies who only expect physical intimacy on the first date, there are also many sugar babies out there who, unfortunately, don’t understand the “mutually beneficial” part of an arrangement and simply try to get as much out of their benefactor without giving anything, such as enjoyable companionship, in return. Which brings me to my next, final and most important point…

Don’t expect sex on the first date!
Although you can certainly have a sugar daddy/sugar baby arrangement without physical intimacy, such as having a sugar baby as a traveling companion, as an escort to work or social functions or as someone to mentor, there is ocasionally an expectation that sex and other forms of physical intimacy will automatically be part of an arrangement from the start. You should never expect sex on the first date with a sugar baby and you should NEVER either attempt to pressure your date into sex because of your generosity on the date or offer to exchange money for sexual favors (that’s not an arrangement, that’s prostitution, which can land you in jail). An arrangement is supposed to be “mutually beneficial,” which means that both parties are to benefit and gain something worthwhile from the experience. Your date isn’t a prostitute, nor should you treat them as such. It’s perfectly acceptable, if the physical and emotional chemistry is there, for consensual intimacy between you and your date. Truth be told, my first sugar baby date ended with us making out in my car, her asking me how far it was to my place and… well, I’ll leave the rest up to your imagination 😉 Just like with a non-arrangement date, sex should never be expected and you should always treat your date with the respect and courtesy that they, as a human being, deserve.

In Brief…
Despite the generosity and companionship that is present in an arrangement, remember that you’re going out on a DATE! This is, first and foremost, an opportunity to get to know someone, have fun, be romantic and see if the potential for future meetings is there. Impress your date and give them the opportunity to impress you in return so you’ll both mutually benefit from the experience!

About cjasher (1591 Articles)
C.J. Asher is a blogger on various subject matters and trending topics related to sexuality, such as prostitution, women's rights, sex trafficking and LGBT issues as well as the adult entertainment industry, having interviewed celebrities such as Dennis Hof and Joanna Angel. C.J. currently resides in Philadelphia, PA and his blog can be found at

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