In the midst of all this change I met a guy who is about 13 years older than I am. He’s married and I guess you can say he’s looking for a little excitement. We don’t have a physical relationship, but he likes spending time with me and likes to give me money and gifts. And he really helped me out when I was going through a rough time. We are friends and, instead of sleeping with him, I try to offer him advice about his family life and working things out with his wife. I don’t find him attractive and he’s definitely not someone I would ever go for, but I stay because of the money. It’s reeeeaaallllyyy easy money. And in some sense I feel good about helping him.
So here’s my current situation: I ended the “sugar daddy” relationship because he crossed the line and sent me flowers at work while my boyfriend was there. I was really relieved to get out of our arrangement because I felt horrible about lying to my boyfriend even if I didn’t have a romantic or physical type of relationship with that guy. But we have thought of a brilliant arrangement, though, that makes me feel a little easier about spending time with him and making some serious money again. I could teach him tennis lessons. That way he can pay me without it looking strange and he can still spend time with me without my boyfriend getting alarmed.
So what do you think? I know I am wrong for lying . . . but would this be considered cheating in any way? — Tennis-Playing Sugar Baby
It depends on what your definition of “cheating” is, but, regardless of whether you or your boyfriend call it cheating, what you’re talking about doing is deceitful and sneaky and those aren’t qualities and issues you should be introducing to a relationship that you hope will be life-long.
And let’s talk about this idea of a life-long relationship with your boyfriend. You say you eventually plan to marry him, but what’s your plan if your boyfriend continues not to “spoil” you the way you want or financially assist you the way you need? Even if you fessed up about your sugar baby gig (and that’s exactly what it is, however you want to slice it. A rich man pays you for your company; that makes you a sugar baby), and even if your boyfriend was ok with the situation, you can’t be a sugar baby forever. For one thing, you will age out of the “baby” bracket faster than you might imagine right now. And even before that happens, something else might occur in your life to change your looks and/or your desirability to prospective sugar daddies in a pretty major way (like pregnancy, weight changes, or simply being married). And what is your plan once you can no longer count on making easy money off rich men and your long-term partner doesn’t spoil you or financially assist you the way you want? What are you going to do then?
I bring up these future considerations because they very much affect the decisions you need to make in the present. If your boyfriend isn’t a long-term fit for you, then maybe it doesn’t matter all that much whether your relationship survives your current money-making scheme. Maybe, if it’s going to end anyway because you don’t believe your needs will ever be met, it’s better if you just end it now. Or, maybe, if you don’t believe that your boyfriend will be able to give you the things you think you want, it’s better if you adjust your expectations and re-prioritize the things you’re looking for in a mate.
Regardless, if you DO decide to continue seeing your boyfriend and you DO decide to pursue this sugar baby set-up, you need to tell your boyfriend about it. You need to tell him that this guy pays you to spend time with him and you aren’t intimate with him and he doesn’t touch you, but he does pay you for your company. Maybe your boyfriend won’t care. But I bet he will. And you know why? Because most guys wouldn’t like the idea of another man paying for their girlfriends’ company. It won’t matter that you don’t screw the guy. It will matter that some dude is paying you to hang out with him. And if your boyfriend truly cares about you, he will worry about this guy’s intentions (and you should be too!) — this guy who has a wife but is paying another woman to be his companion. He will worry about him crossing boundaries and touching you or worse. He will agonize over this guy fantasizing about you, picturing you naked (even if you don’t let him see the real thing), potentially pushing you out of your comfort zone and taking advantage of you because he’s paid for you, after all, and because he’s the kind of guy who is used to getting what he wants (and probably used to crossing boundaries, as he’s already proven when he sent you flowers at work).
You know this is how your boyfriend will likely react (because it’s how most men would react), and that’s why you don’t want to tell him the truth. And your withholding the truth makes what you’re doing, or thinking about doing (and have already done!), every bit as dishonest and hurtful and damaging as “cheating.” Because in the end it doesn’t matter if you plan to not allow this man to screw you. It doesn’t matter if you aren’t attracted to him and that you’re only using him for his money. It doesn’t matter how innocent you make your arrangement seem (“It’s just tennis lessons!”); as long as you keep it a secret from your boyfriend, you ARE a cheater. You are cheating on the basic rules of a relationship, which include being fucking honest about shit, especially shit like getting paid to be some dude’s companion.
So, be honest. Be honest to your boyfriend, and, God, be honest to yourself.
If you have a relationship/dating question I can help answer, you can send me your letters at email@example.com.