Sugar Daddy: Could he be serious about me?

Check out our video on Dating Older Men. 

Dear Guys,

About two months ago I met someone online on a Sugar Daddy Website. It was the first time either of us has ever met up with anyone from the website. Let’s call him Jack. Jack is 39 and very wealthy. His work causes him to travel a lot. He broke off his engagement of about a year back in November. I am 19 and currently a student.

Jack and I have only met up twice so far. Both times we went out to a very nice dinner and afterward we had sex. Jack is a gentlemen in all areas; during intercourse he always pleases me first and if a position hurts he will change it to what he can tell I am comfortable with. Though we met on a sugar daddy website, Jack and I have never made arrangements for pay or anything to make it seem like that type of arrangement. I guess it feels more like casual dating. I once asked Jack what we were doing and he replied “Getting to know each other right now and seeing if we are compatible.”

He texts me everyday since the first time we have talked. Sometimes he will answer right away, but a majority of the time he takes anywhere from an hour to three hours to reply to me. I know he is busy being away for work, but does this mean anything?

I have come to develop feelings for Jack, but I am not quite sure what he is looking for and I find it awkward to ask because of how we met, and also the age difference. I was wondering if you could help me and give me some advice as to what he may want or be thinking? How should I act towards the situation? Also with the communication when we aren’t together with him taking hours to answer me. Should I not answer him right away? Do you think anything serious could ever come out of this? What is your opinion about the situation; any advice you could give me would be great.


Dear Kay,

Thanks for your question.

Taking in consideration the way you met, it’s hard to say how this will unfold. But typically, the nature of a “sugar daddy relationship” is casual, similar to what you describe. Dating and sex. We’re not sure what motivated you to join the dating site, but from a guy’s perspective, he’s probably looking for exactly what he’s getting. Someone much younger he can take out on the town and enjoy in the bedroom when he’s not busy with work—which by the way is probably his first priority. However, having said that, it is possible that some of the men on the site are looking for a younger woman to marry, but not likely.

So we have two questions for you.

If work is his first priority is he still someone you’d like to have a more serious and committed relationship with?

And what initially motivated you to join the Sugar Daddy Website?

The only way to know for sure is to talk to him about it at some point. Let him know how you’re feeling and see where his head’s at. It might be a little too soon for that, but you’re certainly not going to get any answers by keeping your feelings to yourself. And our rule is, if you’re already being physical then the relationship has progressed enough to talk about the future. As far as his response time. No worries. As long as he’s getting back to you in a few hours that’s fine. No need to change your behavior and respond slower, but certainly you can if you want to mirror him.

One thing you can do in the meantime. See if he still has a profile up on the Sugar Daddy site. Not, by snooping, but by using your profile and checking out the site. (We don’t encourage you to go through his phone or computer. That’s not a great way to solidify a partnership of any kind, even though it’s tempting.) That would tell you if he’s at all serious about you, or if he’s still trolling for more women.

Finally, we’d still like to encourage you to date men of all ages—preferably someone a little closer to your age—especially since you’ve expressed interest in having a committed relationship.

We hope this helps a little. Please leave us a comment. We’d like to hear more of your thoughts.

Take care,


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5 Comments on Sugar Daddy: Could he be serious about me?

  1. YoungerGirl // June 25, 2012 at 1:17 pm //

    I met this older guy (I think he’s around 40 and for disclosure I’m 23) about six months ago at a bar in nyc. Neither of us lives in ny. He lives an hour away and I live 4 hours away. So he got us a hotel that first night. We made out. I had originally told him I come into the city about every other weekend, but I am in grad school and so I honestly couldn’t make it into the city as often as I wished. And I wonder, if at first he was interested in making this work because he txtd me more frequently during the first month or so and then maybe he realized I barely come into the city.

    I ended up meeting him for the second time about two months later. And it was really nice we went out to dinner, drinking, and then back to his hotel room. Since this time we will go weeks with out txting though anytime I’m in the city he’s available to meet up. I met up with him for the third time two months after this time and again we got a hotel room. This was the first time he tried to have sex with me and I told him I wasn’t ready to. He didn’t say anything to that. Honestly, I was afraid to have sex with him because too many times in the past once I’ve slept with a guy I’ve seen them lose interest and I’ve become wary of sleeping with them. So this leads to my real question: what exactly is the situation that I am in with him? I guess casual dating would be the best description? But could this be more? Or what is it that he exactly views me as? It just doesn’t seem sustainable that this could go on forever and so I’m not sure how to treat this. This guy is amazingly hot and so he could easily date other girls, so I’m not sure where I fit in.

  2. @Younger Girl…….We think you have a pretty good understanding of the situation. You’re a hot, younger girl that he has a chance to have sex with. He might be hot himself—as you say—but he’s still 40, which makes you at 23 a huge catch. (Believe us, he’s telling all his buddies about the situation.) The thing is, if he actually wanted to have a relationship with you, the two of you wouldn’t just be meeting up in hotel rooms. (Check out our video on the topic. Dating Older Men.) So what do you want from this? It sounds like you want something more than just sex, otherwise you would have jumped at the opportunity. What do you think?

  3. YoungerGirl // June 25, 2012 at 4:57 pm //

    @One of he guys…well we stay at hotel rooms because neither of us lives/have a place in the city. So I’m curious where you think we would be meeting up? Like we go out to dinner, get breakfast the next day, etc. And also I assume because he is so good looking that other girls even my age that actually live in his city would date him, so I don’t understand why six months later he still is interested in meeting up.

    If I lived in the city, I would want to date him. But I know a long distance thing isn’t possible since I have two more years left of grad school. So what I want is just for this situation to continue indefinetly (partly because I don’t want to date anyone in grad school so this would be the perfect situation until I move back to the city). But since I do not know what his end game is, I’m worried that if we have sex that’ll be the end, so I’m not sure how to judge how he sees the situation.

  4. YoungerGirl // June 26, 2012 at 1:10 pm //

    @One of the Guys…Thanks for the words of caution. I think the reason we meet in nyc is that I grew up there and so I come in on the weekends to see my family & friends, and so he comes down to meet me in the city. And the town I live in is a small town in the middle of nowhere.
    Do you think there’s a way to make this something more? Or is the most this can be is just more fun nights?
    Also, do you think the situation would be different if I came into the city more often (which is what I originally led him to believe I did)? For the rest of the summer, I have trips planned to the city almost every weekend and was wondering if I should let him know I’m in town more frequently or only let him know every few weeks? I would like to see him more often, but don’t want to make this too easy for him.

  5. @Younger Girl……We think you should let him know you’re in town more often. If he’s excited about that idea, then he might actually be interested in something beyond an occasional rendezvous. If he starts making excuses, or flat out says he doesn’t want to hang out that much, then you’ll have some more answers. It’s too soon to know. Just be honest, and see what happens. And keep us posted. We are interested in how things progress. Good luck.

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