My Older Man’s Best Friend is an Ex-Girlfriend—How Do I Handle That?

QUESTION: This has been bug­ging me for a while now and I don’t know how to deal with it. I’m dat­ing an older man, and our rela­tion­ship is going really well. But it really both­ers me that his best friend is a woman, and not just that—it’s a woman that he used to date. She’s about my age (me and my older man are 19 years apart) and he insists that they’re just friends and noth­ing more. But I tried, and I still can’t come to terms with it. Am I over­re­act­ing? Do I just have to suck it up? What am I sup­posed to do about this?

CHELSEA SAYS: Hav­ing been in a sim­i­lar sit­u­a­tion myself, I totally get where you’re com­ing from. This is a com­mon prob­lem in rela­tion­ships that always brings up the same age-old ques­tion: can a man and a woman really be “just friends?”

I sup­pose it’s a lit­tle hyp­o­crit­i­cal for me to tell you that his best friend shouldn’t be a woman, because a lot of my very close friends are guys. I do think it’s pos­si­ble for men and women to be friends—it’s very likely that your older man and this other woman tried dat­ing once, but there was obvi­ously some­thing that didn’t work in their rela­tion­ship. Do you know why they broke up? I dated an older man once and we just real­ized that we were more like bud­dies than a cou­ple, so we broke up and today, we’re very good friends. But even though I was drawn to him once upon a time, I don’t feel the slight­est bit attracted to him today.

It’s hard to say whether or not you’re over­re­act­ing with­out know­ing your older man or ex firsthand—it’s a lot eas­ier to read the rela­tion­ship between peo­ple when you see them together.

When I was in this sit­u­a­tion, I ended up being right about my boyfriend—he was hav­ing an affair with his ex. But relax, I’m not telling you that to freak you out. I’m telling you that because there are a few red flags that I missed in my rela­tion­ship that I think you can use. For exam­ple, does your older man’s best friend make an effort to get to know you? If she’s open to being friends with you, you prob­a­bly have noth­ing to worry about. But if she avoids you like the plague and she hasn’t made the effort to talk to you or get to know you, there’s prob­a­bly a good rea­son for that.

Does your older man get really defen­sive when you bring up the topic? If every time you men­tion it, he gets really angry or tries to tell you that you’re being crazy and over­re­act­ing, he might be deflect­ing the atten­tion from him to you because he’s hid­ing something.

At the end of the day, you have to trust your gut feeling—a woman’s intu­ition is a very pow­er­ful thing. If you really don’t think your older man is being faith­ful, then why stay in a rela­tion­ship with a man you don’t trust? Plus, (and this might be painful to hear) if he isn’t will­ing to dis­tance him­self from her after know­ing that it makes you THAT uncom­fort­able, there prob­a­bly isn’t much long-term poten­tial with this relationship.

TRENT SAYS: If only that kind of friend­ship was exclu­sive to “tra­di­tional” rela­tion­ships. But it’s not. Even some sugar dad­dies keep in con­tact with their ex-sugar babies. And the rip­ples of dis­con­tent can be felt far and wide.

The sugar daddy/sugar baby rela­tion­ship can be quite ten­u­ous. If you’re in a rela­tion­ship that has emo­tional and com­mit­ment bound­aries, prag­matic Trent would prob­a­bly say you have to suck it up. How­ever, I can see how and why he being friends with an ex would be hurt­ful. While you may have an exclu­sive arrange­ment with him, what’s to say that couldn’t be taken away from you? After all, he slipped out of his ex-sugar baby’s hands and into yours.

I’m dubi­ous of a sugar daddy who claims he can be “just friends” with an ex. You’re prob­a­bly too young to remem­ber the movie When Harry Met Sally. But I think it’s true—sex always gets in the way of a friendship.

I don’t know your sugar daddy. Maybe he’s entirely trust­wor­thy and on the up-and-up. Regard­less, you’re the sugar baby and your sugar daddy is sup­posed to spend his time ador­ing you. That’s part of the joy of being a sugar baby. That being said, you have two options: either suck it up, or con­front him and see how deep the rela­tion­ship is.

But, if I was going to be more sen­si­tive to your sit­u­a­tion, I would say you don’t need to suck it up on any level. Like any rela­tion­ship, you owe it to your­self to talk to him and tell him how it makes you feel, and that his actions are get­ting in the way of the sugar baby/sugar daddy rela­tion­ship. And make sure he knows you’re not happy. Ask him if it’s more impor­tant for him to hurt you by hav­ing a friend­ship with an ex that’s just a friend than it is to have you happy in the rela­tion­ship. A sugar daddy, a good one at least, doesn’t like it when his sugar baby isn’t happy.