Is My Sugar Daddy Secretly Dating Other Women?

QUESTION: I’m 21 and my sugar daddy boyfriend is in his mid 40s. He buys me expen­sive gifts, takes me out on fancy dates, and he even paid for our lux­ury three-week vaca­tion in Italy. But I’m not only with him for his money. He’s very sweet, charm­ing, and respect­ful, and I think I might be falling in love with him. The prob­lem is that, even though he tells me that I’m the only one, I have a feel­ing he’s been see­ing other women behind my back. How do I find out the truth?

CHELSEA SAYS: Good ques­tion, but it would help to know if he’s mar­ried and has a sugar baby (you) on the side, or if you guys are exclu­sive. If he’s mar­ried, it’s easy for him to cheat because he’s being dis­creet with you, so it’s quite pos­si­ble he could be dis­creet with his sec­ond sugar baby. How would you know?

Have you and your sugar daddy ever dis­cussed the rela­tion­ship being exclu­sive? If you haven’t talked about it, then you can’t really get mad at him for scop­ing out other sugar babies. Unlike nor­mal rela­tion­ships, monogamy isn’t always expected with sugar daddy rela­tion­ships, even if you are start­ing to develop real feel­ings for him. Yes, he’s told you that you’re the only one, but the only one what? Sugar baby? Girl­friend? Future wife?

How­ever, if your sugar daddy does have another sugar baby or two on the side, but is inten­tion­ally keep­ing it from you (which it sounds like he is), then he knows that he’s doing some­thing he shouldn’t be and that’s a red flag.

Usu­ally, I’m all for keep­ing the lines of com­mu­ni­ca­tion open, and if the cir­cum­stances were dif­fer­ent, I would have encour­aged you to ask your sugar daddy directly. But I think it’s safe to say that he doesn’t want you to know about it, so he’s obvi­ously not going to tell you any­thing if you ask. Here are a few ways to try and find out if your sugar daddy is sat­is­fy­ing his sweet tooth some­where else.


• Steal his phone. Snag his phone when you can, like when he’s show­er­ing or sleep­ing. Search through text mes­sages, e-mails, pho­tos, call his­tory, and what­ever else you can. And remem­ber, you’re not only look­ing for unfa­mil­iar names and numbers—it could be some­one you know of, like a coworker.

• Secre­tive cell phone activ­ity. This one’s pretty obvi­ous, but if your sugar daddy leaves the room to answer calls, then eaves­drop on his con­ver­sa­tion. If he secretly texts when he thinks you’re not look­ing, sneak up from behind and give him a big hug. Tell him you just felt like it, but really, you’ll be look­ing over his shoul­der to get a sneak peek. If he imme­di­ately hides his phone screen or gets angry for sneak­ing up on him, that’s a red flag.

• Busi­ness trips. If your sugar daddy is all of a sud­den going on busi­ness trips every other week­end, tell him that for the next one, you’re going to go with him. Even if he’s busy with work, you’ll be there wait­ing for him at night. You’ll be able to gauge by his reac­tion: is he excited, angry, or ner­vous about the prospect of you being there?

• Bills. Check his phone bills for long phone calls with the same number(s). Check credit card state­ments for large pur­chases that never came to you. If you never see the bills because he’s con­ve­niently pay­ing them from work or access­ing them online when he never used to before, he might be hid­ing something.

• Details. If you think your sugar daddy is lying about where he was and what (or who) he was doing, just ask ques­tions. He’ll do one of two things: dodge the ques­tions and glaze over the details, or over­com­pen­sate by giv­ing you too many details. If he gets really annoyed or angry when you ask nicely about his day, he’s prob­a­bly get­ting defen­sive because he’s hid­ing something.

• Sex. Has your sex life dwin­dled? Try spic­ing things up with lin­gerie or role play­ing. If he’s still not feel­ing it, it could mean he doesn’t care because he’s get­ting it some­where else.

• Stake out. This one’s pretty extreme, but des­per­ate times call for des­per­ate mea­sures. Tell your sugar daddy you’re going out of town for a week­end with the girls. Then just keep an eye on what he’s doing while he thinks you’re away.


  • Robert Van Mierlo Jr

    I would love a sugar baby, can some­one hook me up?