In the sugar daddy world, the first official date is truly a major milestone. This is when you really pull out all the stops and attempt to make the most favorable impression possible. The first date also gives you a definitive opportunity to get to know your sugar baby better in an intimate and one-on-one setting.

Now might be a good time to go over the previous sections of this guide to make sure that there is nothing you have missed. The prospective sugar babies that you will go on a first date with have obviously been preselected as part of your shortlist, so they will be your most favorable prospects. At this point, you would have done plenty of research into the characters and backgrounds of each one, so there hopefully won’t be any unpleasant surprises or potential deal-breakers.

The makings of a great first date

There are a number of factors that go toward ensuring a rewarding and fruitful first date:

  • Location
  • Transportation
  • Grooming and attire
  • Topics of conversation
  • Paying for the date


You will want to meet in a place that is accessible to both of you. Unless you live in a remote area or you are both from different parts of the country, it should be a fairly simple matter to find a suitable restaurant or coffee shop in town. You could even meet in a reasonably quiet public spot such as a park or even a museum or gallery.

It would probably be best to avoid meeting in a bar or a club, as those places aren’t exactly conducive to intimate conversation. If you do hit it off at dinner, you have the option to go somewhere else for drinks and/or dancing afterwards.

Things are a bit more complicated if you live far from each other. In most cases, you will be expected to travel to the city where your sugar baby lives. However, you may also arrange to have your sugar baby come to your city, in which case you should be prepared to pay for her hotel accommodations.


In this day and age, picking up the female at her place isn’t absolutely essential. Nevertheless, this might be a good way to score some points. Many sugar babies still appreciate a bit of old-fashioned gallantry, and picking her up with a bouquet of flowers is still an effective way to make a good impression.

If you are unable–or unwilling–to pick up your date, you might opt to arrange for a car pickup service instead. Thankfully, the availability of prearranged car services these days means that you won’t necessarily have to pay for a limousine and driver. If she lives close enough to the place where you will meet, you could even simply pay for her cab.

Needless to say, you should make arrangements to take her home after the date as well. Unless the date has proven to be a complete and utter disaster, you would do well to take her home yourself. You could also arrange for the same car service that brought her to your meeting place. As a last resort, you could simply pack her off into a cab, but unless you handle that delicately, there is a chance that this might be taken against you.

Grooming and attire

Pay close attention to your grooming and attire. You will want to give the impression that you are a successful and financially stable man that has his act together. A two-day growth of stubble, sweatpants, dirty sneakers, and an “Al’s Garage” t-shirt with gravy stains doesn’t exactly scream “success”! Selling yourself as a potential sugar daddy is just as much about dressing the part as it is about playing the part, so dress accordingly.

Topics of conversation

One of the more important aspects of a successful first date is ensuring a steady flow of conversation. Again, going back to the research that you have done into the background and interests of your date will be helpful. Now would be a great time to go over a specific personal characteristic in detail or to ask her about any special interests.

Resist the urge to constantly talk about yourself. Although you will want to make your expectations of the relationship clear, there are ample opportunities to do that some other time. Showing a genuine interest in what she has to say will draw her out and make her feel more comfortable with you. This will also give a better idea of who she is a person, which only works out to your benefit.

Paying for the date

Nowadays, more and more women are not only more comfortable about paying their way on a date, but are more insistent that they do so as well. For better or worse, this isn’t often the case in the sugar dating arena, where many of the traditional rules still apply. You will generally be expected to pay for everything, so be prepared. Make sure that you are still well within your credit card limits, and bring along some cash just in case.

Essential first date etiquette

Some other things that will be helpful to remember are not to drink too much and be gracious and accommodating at all times. A drink or two shouldn’t hurt, but try to resist the temptation to have any more than that no matter how much fun you may be having. Alcohol has the effect of clouding your judgment, which doesn’t bode well for getting to know someone you just met.

Keep your cellphone hidden away on silent mode, and gently suggest that your date do the same. A first date should be a special occasion in which you have both committed to spend time exclusively with each other, so any form of intrusion should be avoided.

Finally, relax and allow yourself to have fun! Remember that the woman you are with is someone who you may be spending a lot of time with, so you will want to be just as comfortable around her as you would want her to be around you.

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