I Went on 3 Dates With a Real Sugar Daddy I Met Online — Here’s What Happened

When you’re broke after having maxed out your credit cards and are wallowing in sadness over a recent breakup with an ex-boyfriend, signing up for a sugar daddy website doesn’t sound like such a bad idea. Besides, you’re single and you have a whole life ahead of you filled with new experiences as a budding twenty-something.
The idea is far fetched, I know. It’s easy to be judgmental. The first time I ever heard of a sugar daddy website was during college. There were rumors about some girl dating a sugar daddy she found online in exchange for expensive designer bags and college tuition.
I judged her disapprovingly because I thought dating someone for materialistic things would be below my own dignity. Thinking back, I was speaking from a point of privilege because money wasn’t really an issue during my undergraduate years. As a recent graduate who has moved home to live with the parentals to figure out life, yeah — money is an issue.
After conducting some online research, I chose what appeared to be a respectable matchmaking website for sugar babies and daddies, Seeking Arrangement. I’ve never known anyone who used these types of dating services so I was on my own as far as advice went.
If you’re a girl, it’s most likely you’ll get an inbox full of messages from random guys who start off conversations that sound like business propositions and make you feel like an online escort.
After only a few days, I received about 30 messages from different men. I finally received a seemingly normal message from a guy on the site. He messaged me with a simple “hey.” He was under 30 and reported his annual income as $300,000. After some flirtatious banter, I concluded that he, whom I shall call James in this story, was well-educated and less creepy than anyone else who messaged me, and so we exchanged numbers.
We texted on a daily basis and I learned that James had graduated from a prestigious Ivy League business school, worked at an iconic investment banking firm and was now a senior executive at a new company. We lived six hours from each other, but James flies down to my city regularly for seemingly important business meetings (so you know he’s the real deal).
We had intelligent convos and he gave me life, career and family advice. Guys on the site are older so they presumably have a wealth of wisdom and knowledge to impart. 
However, one of my biggest pet peeves when on dating sites is having guys I don’t know call me “babe” or “baby.” James started calling me babe in his second text message. We may have had potential, but we weren’t on that level yet.
On another note, if girls want to send scandalous pictures to a guy, they will probably initiate it. So fellas: don’t ask a girl for sexy pics or she’ll send you something stupid like a pic of her cat. James got a lot of pictures of my cat.  
First Date
Nothing is ever set in stone until you meet in person, right? You can hit it off online and over text, but it’s a completely different ballgame in real life. For our first date, James flew down for a business meeting during the day and picked a fancy, intimate Italian restaurant in Beverly Hills for the evening. He waited at the restaurant in his business suit and I was late (stuck in 405 traffic), but he was nice and waited patiently.
I would imagine people would stare and be suspicious if I was with a guy with grey hair, but he was under 30 and looked pretty good for his age. The restaurant was chic and crowded with a bunch of hip Los Angelenos. First dates are always awkward, but alcohol always makes it easier. I had a cocktail; he ordered bourbon or scotch. James must have been nervous or wanted to get me drunk because we had a whole bottle of wine after (but I can hold my liquor so it’s all good).
I’ve never been on a date where money wasn’t an awkward issue. The idea of having whatever I wanted and as much as I wanted was pretty exciting. I went a little crazy and the server gave me funny looks when I ordered eight different appetizers and an $80 T-bone steak.
You’d be impressed by how much I can eat. That was probably the best steak of my life and I didn’t have to feel guilty about spending that much money on food. I was so full, I didn’t even touch my dessert — and I LOVE dessert. James was nice and didn’t judge me for eating everything. Our bill came out to nearly $400, but he didn’t even sweat it. I just looked away and sipped the rest of my wine as he paid the bill.
At the end of the dinner he told me he had bought me a gift. I made nervous chatter as we walked to his car. He reached into his car and pulled out a fancy looking bag with a bow on it. I thanked him and leaned in for a hug as he leaned in for a kiss. I don’t kiss guys on the first date so I turned my head at the last second and he ended up awkwardly kissing my cheek.
Second Date
We chatted almost every day after the first date. James eventually offered to fly me up to meet him several times, but I declined.
Two weeks later, James had another business meeting in town so we went on our second date in Newport Beach. It was another four dollar sign Yelp restaurant because those are the only kinds of restaurants he ever suggests. I had the best scallops of my life and indulged myself in the most decadent seafood like prawns, clams, mussels, and lobster tacos — the list goes on. 
James always seemed to be wearing business suits like he just got out of a meeting or something. While eating our surf and turf, we talked about what was going on with my life and I asked him how his business meetings went. James always answers vaguely because he says his banking meetings involve confidential client information. Our bill came out to around $300.
At the end of the date, he didn’t try to kiss me like last time and in our texts afterwards, he actually scaled back on hinting about trying to get in my pants. I kind of felt like I had him in the palm of my hand.
Third Date
Almost a couple weeks after the last date, James was in town for a business meeting again and we went to a fancy American restaurant in Santa Monica on a Friday. I stopped looking at the bill because I knew I probably couldn’t pay it with anything in my bank account anyways. After dinner, we went shopping in Hermès — James wanted to pick out something for himself. When James asked me if there was anything I wanted, the voice in my head said “DUH EVERYTHING.” In real life, I said no because I didn’t want to be too greedy.
Even though we had made plans to hang out on just that Friday, James had apparently rented out a whole place on Airbnb for the entire weekend and was pretty presumptuous about me staying with him. I didn’t like that at all and he made his disappointment known when I told him I wasn’t down.
It’s nice to have someone dote on you and feel like you will be taken care of financially especially when you’re completely broke and not sure what you’re doing with your life. However, I couldn’t help but feel as though there were unwarranted expectations and a lot of strings attached to this sort of relationship.
In the week after what would be our last date, James bombarded me with more texts to meet up. He became distinctly clingy, constantly bringing up that he wanted something more than just companionship and friendship. When I wasn’t ready to reciprocate, I dropped the “let’s remain friends” bomb. He texted a few more times afterwards, probably to see if I still felt the same way, but eventually he disappeared altogether.
Perhaps I would have been more willing to pursue it had there been more chemistry between us, but I didn’t want to keep leading him on for free things and free dinners.
Overall, I had fun and I enjoyed his company. When you’re in the dating game and on a site such as Seeking Arrangement, it’s important to keep an open mind. Like most dating apps, you will find people who are only “DTF” and want something purely physical and sexual. However, there are a handful of people who are looking for a meaningful connection, even if the relationship is a bit unconventional.
Who’s to say or judge what a normal relationship should be anyway? If you’re playing around with the idea or even curious about signing up, I would say go for it!
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