Is My Older Boyfriend Going to Cheat on Me with His Ex?

QUESTION: I’m dat­ing this older man who’s sep­a­rated from his wife—they’ve been sep­a­rated for about a year now, but they’re not legally divorced yet. He just told me he’s going to Maui with his ex-wife and their two young kids for the hol­i­days; he says it’s an annual fam­ily tra­di­tion and they want to con­tinue it for their kids’ sake. He also assured me that they would be stay­ing in sep­a­rate rooms. I’m try­ing not to get crazy jeal­ous, but do you think I should be worried?

CHELSEA SAYS: I don’t blame you for being jeal­ous, but unfor­tu­nately, I think this is one of those cases where there isn’t really much you can do, espe­cially since it sounds like he was telling you, not ask­ing you. And since you’re the new woman in his life, you don’t really have much ground to stand on in terms of ask­ing him not to spend time with his ex-wife and kids.

If I was in your shoes, my biggest cause for worry would be the fact that your older man and his ex-wife are sep­a­rated and not divorced. Do you know why they’re putting off a divorce? Do you know why their mar­riage ended in the first place? If you don’t know the details, that might be some­thing you want to try and talk to him about, just for the sake of your own rela­tion­ship. If he’s hold­ing out for rec­on­cil­i­a­tion with his wife and is just keep­ing you around to pass the time, then I imag­ine you’d want to know sooner rather than later.

Also, I hate to tell you this, but if he’s look­ing to get back into the sack with his ex-wife, he doesn’t need to be in Maui with her to do it. I think this really boils down to trust between you and your boyfriend. The fact of the mat­ter is that he’s got an ex-wife and two kids—that’s never really going to go away. In order for your rela­tion­ship to ever work, you have to be able to trust him, and trust the fact that he wants to be with you and won’t do any­thing to ruin that.

If the jeal­ousy is too much for you, then maybe you should recon­sider this rela­tion­ship. Why put your­self through the grief? But if you do decide to power through and give your boyfriend a chance to prove him­self, then try not to obsess over it while he’s away. Being a woman, I know that sounds vir­tu­ally impos­si­ble. But keep your­self busy—hang out with friends and fam­ily; enjoy the holidays!

TRENT SAYS: I think this is one of the hur­dles cou­ples in gen­eral face when they date or marry some­one with a fam­ily from a pre­vi­ous rela­tion­ship. On an aca­d­e­mic level, it’s great that he wants to go to Maui and keep things even-keeled and seem­ingly healthy for his kids.

On a prac­ti­cal level where emo­tions exist, it’s not the most con­ven­tional Christ­mas sit­u­a­tion. And I don’t think any­one would think it’s odd that you’re jeal­ous; in fact, it would seem odd if you weren’t a tiny bit jealous.

Jeal­ousies aside, why are you wor­ried about his trip? Has he given you any rea­son to be wor­ried? Or were you worried/anxious/nervous about his ex when you first started to date your sugar daddy?

For­tu­nately, you’re a year into the rela­tion­ship, so you should have a good feel­ing about where your rela­tion­ship with him stands. Is he the kind of per­son who would throw away a great rela­tion­ship with you to be inti­mate with a woman he went out of his way to dis­tance him­self from?

I’d say you should talk to him and tell him about your wor­ries and that hope­fully he’d put those fears to rest (and you should), but I’m guess­ing that even if he says all the right things, you won’t really be feel­ing rested and con­tent until he comes back.

There’s no doubt it’s a tough sit­u­a­tion to be in, but aside from you accom­pa­ny­ing him on the trip, you’re going to have to just trust him and your rela­tion­ship. And show him how much you love him when he returns home to you!