What Do You Do When You Realize That You’re Falling for Your Sugar Daddy’s Best Friend?

dating_a_sugar_daddy_september5_13QUESTION: My older sugar daddy recently intro­duced me to his busi­ness part­ner, who also hap­pens to be his best friend. A few weeks ago, the three of us were sup­posed to have din­ner, but my sugar daddy got held up with a client and couldn’t make it—so, it ended up being just me and his friend. We’ve been talk­ing on the phone every night since. It feels ter­ri­ble to admit, but I think I’m start­ing to really fall for my sugar daddy’s friend. What should I do?

CHELSEA SAYS: If you’ve already started talk­ing to this other guy every night, it sounds to me like you’ve already kind of made up your mind. If you’re in a rela­tion­ship and you’re build­ing feel­ings for some­one else, then some­thing is obvi­ously not right in your cur­rent rela­tion­ship. You need to fig­ure out what the prob­lem is and if it can be fixed. If it can’t be fixed, then you need to break up with your sugar daddy sooner rather than later, before things get even messier. The last thing you want to do is be the rea­son their busi­ness rela­tion­ship and friend­ship is destroyed.

If you decide that you want to stay with your sugar daddy and work on your rela­tion­ship, then you need to imme­di­ately stop talk­ing to his friend, because it’s not at all appro­pri­ate, espe­cially if it’s behind his back. You’re just going to cre­ate more trou­ble for your­self in the long run.

If you do decide to leave your sugar daddy and pur­sue the other guy, make sure it’s worth it because, in all hon­esty, it’s not going to be easy. Your sugar daddy prob­a­bly isn’t going to be too open to the idea of you two hook­ing up, so ease into it. Give him some time to get over the break-up and don’t be mali­cious about it—try to end the rela­tion­ship on good terms. Admit­ting to your sugar daddy that you’re in love with his best friend prob­a­bly isn’t the way to go. Just tell him that you don’t think you’re as com­pat­i­ble together as you thought and that you want to be hon­est and not lead him on any­more. Don’t give him any rea­son to resent you or his friend. And, of course, if you’re going to break up with your sugar daddy for another guy, make sure the other is actu­ally inter­ested and isn’t just being nice to you because you’re his buddy’s girl.

TRENT SAYS: For starters, any rela­tion­ship, whether it involves a sugar baby/sugar daddy or it runs along more tra­di­tional lines, takes work. Even when things are going smoothly, you have to make an effort. On top of that, chances are really good you’re going to go through life and meet older men you find more attrac­tive and even wealth­ier than your sugar daddy. You need to decide whether or not your cur­rent arrange­ment is work­ing for you. If not, move on. If so, then work on it. Oth­er­wise, you’ll be for­ever chas­ing greener pastures.

That said, it sounds like you might be look­ing for a change of scenery. I say this because the tra­di­tional sugar daddy/sugar baby agree­ment has strict boundaries—once those bound­aries are crossed, it gen­er­ally means that you’re get­ting bored, and it’s prob­a­bly best to just move on. And by that, I mean to some­one other than your cur­rent sugar daddy’s busi­ness part­ner. Clearly, your sugar daddy and his busi­ness part­ner have issues. Why else would his part­ner (and friend) think it’s OK to talk to you every night behind your sugar daddy’s back? But that’s a totally dif­fer­ent issue.

This is inter­est­ing, though, because it high­lights one of the risks of being with a sugar daddy and vice versa. If he tires of you, he’ll dump you for some­one else. At the same time, because of the nature of the rela­tion­ship, you can just as eas­ily leave him if you find an older man who you con­nect bet­ter with.

It may sound self­ish, but you have to look out for your­self. And what I hear you inad­ver­tently say­ing is that you think you’re worth a lot more. If you are, then you should have no prob­lem find­ing another sugar daddy.