(Sugar) Baby's First Date

by Charlotte O’Dair


On a recent Wednesday, my friend Annie1 went on her first date with a man she met through SeekingArrangement.com, the self-proclaimed “leading Sugar Daddy dating site.” Annie, a “Sugar Baby,” has been looking for what the site calls a “mutually beneficial relationship.” In exchange for companionship, the perks for Sugar Babies can include “financial stability,” “experienced men,” and being “pampered.” A day after her date with a Sugar Daddy, she told me about her experience.

James2 was one of the first people I talked to on SeekingArrangement. There are a lot of guys who just trawl the site for the second there’s a new profile to instantly favorite and message; that makes you feel adored, because you’ve literally just made an account, and then you feel like, “Oh my god! I’m so popular already!” But James just looked at my profile and didn’t do anything. I checked his profile and thought it was funny, so I was offended that he hadn’t said anything to me. So, I messaged him; I very much pursued him because I was pissed that he wasn’t paying attention to me. His original messages were pretty removed and not the most authentic seeming, so I just kept chatting him and trying to tease it out. Then it became this thing where he was clearly being much more authentic than I was, or, at least, appearing to be.

We talked for a solid month, at least, maybe a tiny bit longer. The original plan was to meet for drinks on Monday, go shopping, eat a nice dinner, and then probably get drinks at the bar of the hotel where he was staying. He messaged me to try to meet at an exceedingly fancy restaurant on Tuesday night, which I wish I could have done, except he ended up having a meeting with a celebrity. So, we just got drinks at around eleven on Wednesday, at the hotel bar, which was very chill and swanky. I walked into the lobby, where we had agreed to meet. I didn’t see him, and I was definitely the youngest person there. All of a sudden he appeared and was just like, “So, you’re here!” He was dressed really nicely, in a button-down shirt underneath a blazer, slacks and horn-rimmed glasses. He was very, very metrosexual, which surprised me because I’d imagined him as this pretty manly, kind of goofy dude. He was gentlemanly and pulled out my chair when we sat down at the bar.

I tried very hard to make sure we sat close, but also to make sure that ours knees wouldn’t touch — I didn’t want to do anything even remotely intimate, because at that point I had no idea how I felt about the entire situation. James kept complimenting me and telling me how glad he is that we could meet up because I’m always out doing something or meeting someone and how charming he thinks it is that I’m so social. The weirdest thing about it was how it was just like, pretty normal in terms of what we talked about. We talked about movies, art museums, the housing market, and his job. It came up that his real name wasn’t James, it’s Alan3. (I found out his last name as well, because he said it when he set up the tab at the bar, and it turns out that he’s totally Googleable: He’s really what he says he is on his profile and teaches at an Ivy League university.)

We had like a couple drinks — well, he was still working on one drink and I’d had three — when James casually mentioned that he and his wife have this arrangement where he can see other people while he’s traveling for work, but not when he’s at home. At this point James was like, “Oh my god, I don’t want to forget, let me give you cab fare!” Before we met up, over text, I had made all of these intimations about him giving me “cab fare” — trying to hint at money for my time, not actual cab fare, which I thought he understood. But he was clearly more of a noob than he was willing to admit. He took out his wallet, and I could see that he’s got like two hundreds, a fifty, and a bunch of smaller bills. He handed me the fifty, and at that moment, I thought, “Okay, he doesn’t have more than two hundred dollars in cash on him, there’s no way I’m fucking him tonight.” Honestly, for shoes, I would’ve probably considered having sex with him very, very seriously. But we didn’t get to go shopping together, and I’m not going to go upstairs to his hotel room with him and have him give me two hundred more dollars to do something I’m not super comfortable with. I know that if we had met under any other circumstances I wouldn’t still be fawning over him.

I thought that James would want to ignore the fact that we’d met through this weird mediated site, but he wanted me to tell him about the other people I had met through SeekingArrangement. I guess that’s what people who meet on the internet do — they talk about the internet. If it were OkCupid or JDate, we’d probably be doing the same thing. But it was kind of weird that he made it a point to say that although he was curious about what other men’s SeekingArrangement profiles were like, he never looked at them, because he “certainly didn’t want anyone to think he was gay.” He said that he had gotten a lot of offers from prostitutes over SeekingArrangement, but that’s not what he’s interested in — he wanted someone he can talk to. He went on and on about how he knew how elitist he sounded, but, he said, “How long of a conversation can I hold with a nail technician that’s coming in to meet me from Staten Island?” He also talked about how he had tried dating eighteen-year-olds off of SeekingArrangement, and how “they just weren’t on the same level of maturity.” But, he added, “It’s so crazy what happens to a female in the span of three years.” He asked me about my age threshold — like, how old I would go. I just said late forties, because I thought he was in his early or mid-forties. He looked kind of upset, then immediately asked, “How old is your father?”

As the night wound down, James started moving his chair closer to mine, touching my leg. I wasn’t doing anything back, but I let him take my hand when he reached for it. Later, he asked me, “Is it ok that I’m holding your hand?” and I was like, “If it wasn’t, I wouldn’t have given it to you.” I could tell he was directing the conversation to try and figure out if I was going upstairs with him or not, because it was the only time he even mentioned compensation in exchange for my companionship. He asked what I got when I met guys from Seeking Arrangement and spent time with them; I lied, and told him that I normally got shoes or clothes or jewelry. He kept touching my hand and my leg, and making comments about how I was sexy and pretty and whatever.

Eventually, James asked me to get the attention of the waiter, and said, “Don’t even look at me, pretend I’m not even here.” The bar was packed and I could barely see this waiter, but what I can see, out of my periphery, is James like, literally licking his lips while rubbing my thigh. It was kind of a turn on, I guess, but it also didn’t seem like he liked me that much or thought I was that special. It was more like he was just in awe of the fact that I was a real person who was right there, sitting in front of him. So I tell him that I’ve got to go, and get up and put my coat on. We kiss goodbye, on the mouth, but it’s the most transactional mouth-to-mouth kiss I’ve ever had. It was nice, and like, sensual, but it was very quick, four seconds max — not a peck, but a short kiss.

James walked me out to the cab, and I was just like, “Fuck!” because I wanted to take the train and keep the fifty bucks. We kissed one more time, but it was the same kind of little goodbye kiss. James asked me when I was leaving the city to go back to school, and I asked him when he’d be back in the city again. He kept saying, “So, I hope you want to see me again,” and I was like, “Yeah, no, I think I do want to meet up again.” He said, “I hope you’re not just saying that but also like, of course, you might just be saying that, because you’re not going to be saying anything else to me right now,” and laughed. I got in the cab, had it take me two blocks to the train, then took the train to this party my friend was throwing.

I ended up dancing with this gorgeous guy at this club, and giving him my number. We were making out on the dance floor for like ever. The time that I spent with James was pretty much the first real date I’ve ever been on, but I feel like it was almost belittled, because I went straight from my date with him, which was a weird experience in a lot of ways, to these very twenty-one-year old things. The date was fun and exciting, but is it more fun and exciting than these very organic things that happened?

James texted me later that night when I was at this party, asking me how it was. My phone died, so I didn’t answer him. I still haven’t answered him. I just can’t figure out if I should keep playing into this thing. It was far less glamorous than I imagined. I wound up with fifty dollars minus eight bucks for cab fare — around forty two dollars, which I spent yesterday and today on like food and beer. If he had given me eight hundred dollars when he gave me cab fare, then I absolutely would have gone up to his hotel room after. I really think I would have. I could definitely have sex with him. Even though it would be easy for me to just leave the bar with the money like I did this time, I would want to do something for him, to avoid feeling guilty about getting this large sum of money from this potentially sad man.

I feel like if I say goodbye to James now and never answer his text messages ever again then it’s pretty harmless. But, if I do meet him again, then it’s not harmless, because if I meet him again, I want to know exactly what’s happening. If like, there’s another weird moment where he cancels on shopping and wants to meet for drinks, will I do that? Will I say to him, “I need more to sleep with you because I’m not actually attracted to you and I need you pay me to make up for that”? It gets really messy.

I had it in my mind in such a TV show way, but James was just a very normal man. He didn’t have any particular game; he wasn’t particularly attractive; he wasn’t particularly nice to me; and he also wasn’t particularly good at this whole arrangement thing. I feel kind of bad about the fact that I didn’t like him, because he was a very nice guy and clearly did not get what was going on. I think if we go out again, he would take me to a nice restaurant and treat me well in that way because he paid for like, four whiskey sours at that hotel, which I’m sure were at least fourteen bucks a piece. But he’s definitely not just going to give me gifts; it’s silly to expect that he would. It’s just weird, because it is so romantic and the idea is that it’s not transactional — but this date was a strange in-between. If he had been much more forthcoming by like, telling me I was so amazing and that he wanted to spoil me, I think I would have been more apt to play into the fantasy as well.

I’m removed enough from romance and definitely a manipulative enough personality that it would be interesting and maybe not super damaging. I feel — and this could be a completely inflated sense — but I feel like I’m enough in control of what I want to do with my body and with my like “sexuality” that I won’t cross any personal lines. I’m sure I could be proved wrong very easily, but it was just really fun to be on this website where men who I could imagine marrying wanted me now, especially when I was still in school, where I’m so sex starved and feeling so ugly and small and shitty constantly. I know the attention I’ve gotten on SeekingArrangement is so artificial and has nothing to do with me as a person — it’s just me as this like, avatar. But it still felt really amazing — like, “Wow, it doesn’t matter if these guys are really creepy, it’s crazy that hundreds if not thousands of people have clicked on my profile.” It’s just validating.

In my own weird little threshold of checks and balances, I feel like having a shitty time with someone who’s our age hurts more, because it feels more like the problem is me.
With someone older from SeekingArrangement, it’s very easy to deflect onto the age difference as the problem or like, “Ugh, he’s a dirty old man.” When a boy at school is not super great to me, and I fuck him and it’s a weird time, it feels really awful and sad. I feel like this is pretty harmless. It feels very low stakes, what with the fake name, the fact that I don’t live in New York ful- time — and even if I ever do move to New York, my parents don’t live here — so it feels like this space where I can be young, and me, and figure out who I am, because it’s so anonymous.

In my dream world, I’ll end this time in New York and the corresponding dating experience having netted enough cash to not have to work on campus next term, to cover my booze, weed, and assorted other recreational drugs, and like, have a new pair of shoes and maybe a fur stole or small fur accessory that’s somewhat attainable. A new fur coat would be the real dream — but I don’t expect any of that to happen. Actually going through with this made me realize that, if I collect fifty bucks in cab fare each week — or, forty two dollars after I ride the cab for two blocks in Midtown — that’s still pretty okay. You know, that’s still grocery money.

Now I’m trying Tinder and seeing how that is. I’m going to try and make some Tinder dates this week. But even on Tinder though, I catch myself being like “This guy looks like we could go somewhere exciting together,” or like, “I don’t think I’m going to go on any fun dates with this dude.”

This interview has been edited and condensed for length and clarity.

Photo by Leslie Kalohi

1. Not her real name

2. Not his real name

3. Not his real real name