QUESTION: I am 55 and just started dating a 23-year-old college student—this is my first time trying this. We hit it off right away and have already had a lot of fun together. However, I am married so we have to be very discreet. Plus, because of my situation, I can’t support her enough financially to meet her expectations. So she has been honest that she can’t be in an exclusive relationship as a result. She is also coming off a sugar baby relationship that ended suddenly, leaving her with bills to pay, so she doesn’t want to put all her “eggs in one basket.” Since we can’t be together all the time, it drives me nuts thinking she might be on other dates, but I have asked her to never discuss other sugar daddies she might be seeing. I’m not worried about guys her own age, as I really believe she enjoys older men. How should I deal with my insecurities and what do I need to do to turn this into a more serious relationship? By the way, I think I am in love with her.
CHELSEA SAYS: There are a lot of things to address here. First of all, with regards to how to have a successful relationship with a younger woman, you really need to take a step back and really look at the situation you’re in. For starters, it’s a little unreasonable (and unfair) to ask your new girlfriend to be exclusive, when you yourself are still married. At least she’s being honest with you about it.
By no means am I saying that you should go and divorce your wife tomorrow, because, in my opinion, what you’ve got going with this younger woman sounds more like an age gap hookup than a genuine age gap love story—it’s a May-December affair. Would you still be so “in love” with her if she wasn’t young, hot, and kind of hard to get?
This younger woman is moving from one sugar daddy relationship to another—she sounds more like a career sugar baby than a serious girlfriend/wife material. Those are two very different things. If she’s a pro sugar baby, she probably has no interest in maintaining a more serious age gap love affair with you. As much as it might hurt to hear, I’m guessing she’s probably perfectly happy getting what she can from you, financially or otherwise, and then moving on. I can understand why not being able to spend more time with her is frustrating for you, but to be honest, it’s nothing personal. It’s not like she’s maliciously going out and dating other sugar daddies just to get to you. It’s just the lifestyle, and you can’t really blame her for not putting all her eggs in one basket, especially if you can’t provide her with everything she needs.
That being said, how serious a relationship do you want? There’s only so far you can take this, considering the whole fact that your May-December affair has to remain discreet. I can’t really tell you how to turn this into a “more serious relationship” until you figure out what exactly you mean by that. Do you want her to stop seeing other sugar daddies? Are you willing to risk your marriage for your younger girlfriend? If she were to cut off ties with her other sources of income, namely her other sugar daddies, are you able to provide enough for her to make ends meet? You need to be able to answer questions like this, because there’s a good chance that your sugar baby might ask you the same sorts of things.
TRENT SAYS: Congratulations on being in an age gap relationship! Being a sugar daddy can be fun and rewarding. It can also be fraught with disappointment if you don’t understand the boundaries that go hand-in-hand with being a sugar daddy. And you seem to be facing a few hurdles early on.
Here are the issues. You’re having a discreet relationship with a younger woman where finances are an important element. She clearly has a background as a sugar baby and knows what the expectations and boundaries are. For her, the relationship is emotionally and physically non-committal, meaning she understands that if you cannot meet her needs, she will keep her options open. That’s the life of a sugar baby.
You are assuming the role of the sugar daddy, since it appears as though her monogamy is based on certain needs being met. But that sounds like it’s a bit of a challenge for you right now. That’s not the life of a sugar daddy.
Here’s how I see it. You are expecting her to live up to age gap relationship guidelines that you yourself cannot adhere to. You’re married, but don’t like the idea of her being with other men. You also want her to wait patiently in the wings for you even though she is finding it difficult to make ends meet. And chances are good she could have her needs met elsewhere.
For example, she may very well be looking at you thinking, “He could be doing much more to help me make ends meet, but instead, his actions show me that I am not his main concern, his family is. Why should they be provided for when I’m not?” It doesn’t sound to me like she’s willing to sacrifice if you aren’t.
When it comes to your growing attached to her, this is where things get complicated. If you find yourself getting attached, you need to step back and think about what it means to be a sugar daddy (if indeed that’s what you think you are); how you two met and the initial expectations about your non-committed age gap relationship. That’s the joy of these kinds of relationships, because there’s no emotional attachment or long-term expectations. You are free to end it without dealing with the baggage. But that’s not really the case here. It’s going to be pretty difficult to find common ground, and by that I mean a scenario where your relationship with her is mutually valuable (and devoid of jealousy).
It takes work to keep an age gap relationship healthy in the best case scenario. So, when you find yourself in a situation where the relationship with the woman you love has obligations or needs that you cannot provide or meet—and you’re jealous that she’s keeping her options open by seeing other men—the chances of success are pretty dim.
How do you turn this into a more serious relationship? I’m not sure that’s what either of you want. It sounds like you’re really attracted to her, enjoy her company, and have fun with her. But it doesn’t sound like the emotional groundwork is there for a truly serious relationship. It sounds like you want her to be there for you no matter what. But she doesn’t see you as doing the same thing for her. She has her expectations and if you can’t meet them, she’ll find others that can. Just like what we do in a so-called traditional relationship.