How Do I Ask My Sugar Daddy About Money on the First Date, and What Are the Rules About Sex?

QUESTION: I’m a first-time sugar baby, and it couldn’t come at a more per­fect time. Well, long story short, how do I ask my sugar daddy for $7,500 on the first date? Do I even ask him that? And do I have sex with him on our first date?

CHELSEA SAYS: Money and sex are two very dif­fer­ent issues, and I think they def­i­nitely need to be addressed on sep­a­rate occa­sions. So, let’s break it down.

Sex on the first date isn’t nec­es­sar­ily out of the ques­tion. It really depends on the nature of your rela­tion­ship and how com­fort­able you are with your new sugar daddy. You’re never oblig­ated to have sex with him at all if you don’t want to. The beauty of sugar/daddy sugar baby rela­tion­ships is that you get set the terms of your rela­tion­ship. You get to decide what you want out of it, and what you are and aren’t will­ing to do to get it. Some cou­ples tend to be more sex­ual, while oth­ers don’t have sex at all.

That’s really some­thing you have to fig­ure out with your sugar daddy. If you have that con­ver­sa­tion with your sugar daddy right off the bat about what the dynam­ics of your rela­tion­ship will be with regards to sex, then you don’t have to worry about com­ing on too strong or being judged for being “easy.” It really just makes life eas­ier for both of you.

Now, about the money issue—don’t ask for money on the first date if you’re plan­ning on hav­ing sex with your sugar daddy. Even though your sugar daddy may not tech­ni­cally be pay­ing you for sex, your ask­ing for money like that on the first date can eas­ily be mis­con­strued as pros­ti­tu­tion, and that’s not what sugar daddy/sugar baby rela­tion­ships are about.

I under­stand that you’re expect­ing some mon­e­tary gains out of the rela­tion­ship, but I’d wait until after the first date to bring it up, espe­cially when you’re ask­ing for that much. Again, this goes back to hav­ing that open line of com­mu­ni­ca­tion with your sugar daddy. You want to know going into it what his spend­ing bud­get is like when it comes to his sugar baby—that way you know not to ask for more than what he’s will­ing to give you. It also gives you the oppor­tu­nity to voice your expec­ta­tions out of the rela­tion­ship, so that he knows what he’s get­ting into as well.

Here’s what it boils down to. You want to keep it classy, so be care­ful not to toe the line between being a sugar baby and an escort. Sugar daddy/sugar baby rela­tion­ships aren’t based solely on sex and money—there still has to be a legit­i­mate con­nec­tion between the two of you.

TRENT SAYS: Indeed, those are the loaded ques­tions of a first-time sugar baby. I’ll be blunt; the sugar daddy/sugar baby rela­tion­ship isn’t based on, “pay me X amount of money per month and I’ll sleep with you.” That’s some­thing com­pletely dif­fer­ent and not some­thing I can really com­ment on.

The sugar baby/sugar daddy rela­tion­ship is about will­fully ful­fill­ing the needs of each other with some­thing that you can eas­ily give. It’s not really that dif­fer­ent from know­ing your wife likes flow­ers and send­ing her a bou­quet every week.

In the case of a sugar baby/sugar daddy rela­tion­ship, you’re just “fast-forwarding” to that phase. But, from a guy’s per­spec­tive, I still need to get to know her first. For exam­ple, on a date I might hear that a young lady has a pen­chant for Gucci purses or Cartier watches, or that she likes to spend her time relax­ing on the beach. This is some­thing that I would keep in the mem­ory bank. I wouldn’t expect any­thing in return but the atten­tion and respect that comes with help­ing ful­fill that need.

Nat­u­rally, of course, I would want her to reciprocate.

If I hear some­thing is unrea­son­able or some­thing that makes me feel uncom­fort­able, I will sim­ply say no. I sup­pose, at the begin­ning, that’s the beauty of these kinds of rela­tion­ships. There’s no emo­tional bag­gage or long-term expec­ta­tions, so if it doesn’t work for me (or for her), I can just move on.