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.”