What to Do When You Realize You’re Dating Your Friend’s Dad

QUESTION: I know my sugar daddy has kids, but I haven’t met them yet because we’ve only been dat­ing for a cou­ple months. The other day, he was telling me some­thing about his daugh­ter, and to show that I was inter­ested in his fam­ily, I asked more about her. He went on and on about how great she is and then showed me a recent pic­ture. Here’s the kicker: I’m 99.9% sure that I used to be friends with this girl in high school back in the day. I didn’t say any­thing to my sugar daddy, but I’m prob­a­bly going to have to meet her even­tu­ally. How do I even begin to deal with this?

CHELSEA SAYS: Wow, talk about a small world. This one is tricky. It would be dif­fer­ent if you and your sugar daddy’s daugh­ter just went to the same school because then you could just pre­tend like you don’t remem­ber her. But if you used to be friends, it’s a lit­tle hard to act like strangers.

It isn’t uncom­mon for an older man to have kids, but it gets com­pli­cated when the kids are about the same age as you, let alone when you know one of them from your past. There’s really no right answer to this, but I can tell you what I would do in your situation.

If and when you do meet her, there’s no doubt it’s going to be awk­ward, unless, of course, she pre­tends not to know you. But in any case, I would tell my sugar daddy if I were you, and there are a few rea­sons why. First of all, it’s only going to make it more awk­ward if he finds out at the same time as his daugh­ter, espe­cially because he showed you her pic­ture. He knows you’ve seen her face before, so if you act sur­prised on the day of, he’ll know you’re putting on a show.

Sec­ond of all, if your sugar daddy knows about your con­nec­tion with his daugh­ter, he can help you deal with it. You can openly dis­cuss it and even ask him directly if she knows there’s a much younger woman in her father’s life. Your sugar daddy might even be will­ing to give his daugh­ter a heads up, just so that it’s that much less uncom­fort­able when you finally do come face-to-face.

Another rea­son I’d con­sider telling him is because if this is going to be a deal breaker for your sugar daddy, you prob­a­bly want him to know sooner rather than later. I know you didn’t scope out an old friend’s dad on pur­pose, but the whole sit­u­a­tion might just be too weird for him, which is under­stand­able. If that’s the case, it’s bet­ter to pull the plug on your rela­tion­ship now, before you go through the whole process of meet­ing his kids.

TRENT SAYS: Wow! This has the mak­ings of an ABC After-School Spe­cial. So, where and how to begin…

For bet­ter or worse, you need to break the ice and tell your sugar daddy that you went to school with his daugh­ter. You could either be straight up with him about it and just tell him, or be more cre­ative. Tell him you want him to know more about your most enjoy­able, infor­ma­tive years. Sit down with him over a glass of wine, pull out your high school year­book, and start to reminisce.

Clearly, you can’t act sur­prised when you come across her pic­ture, since he already showed you her pic­ture. But you can set it up in such a way that you want to show him something.

You have to be aware that your sugar daddy might find this a lit­tle off-putting. After all, it’s one thing to date a much younger woman; it’s another to know that she sat next to your daugh­ter in his­tory class, or was her part­ner in gym. At the same time, it’s bet­ter that he find out now rather than a few months down the road. He deserves to be the one to decide if he’s OK with it or not.

It’s also impor­tant to remem­ber that these are the kinds of dynam­ics that can come up when you date some­one younger or older. He must already know how old you are, and he obvi­ously knows how old his daugh­ter is. So, it can’t be entirely unex­pected on his part.

Just tell him it’s not a deal breaker if she doesn’t call you “mom.”