Business Casual

This sugar business finally got real. I had my first date (if you want to call it that) on Monday and it’s safe to say that it was not what I expected at all. I started talking to this guy, I suppose we’ll call him Coach, about two weeks ago. He wanted to meet up pretty quick after we started to talk and I was fine with that since many of the other guys I’ve talked to never seemed eager to meet up in person and just wanted a chat buddy. It sort of worked out perfectly and we decided to meet up for lunch in Chicago on the 22nd. Having went to school up there for a year, I still have friends that live up in the city so I got to catch up with them as well as meet this guy. Before I made my two and a half hour to Chicago, all I knew at the time was that we were meeting up for lunch at 1 PM, which is important to note for later on. I had texted him on Saturday to confirm lunch and I got a simple reply and that was it…fine…whatever.

Fast-forward to Sunday afternoon after I’m already in Chicago in my friend’s apartment, and I’m finally told where we were going for lunch. 1 PM reservations at a restaurant in a hotel downtown in the loop. Dress code? Business casual. Well that sure would have been nice to know before I left my house. After my friend and I struggled with what to wear with what I had for this lunch meet up, we finally decided on my dark jeans, little wedge booties, a black top, a black blazer, and a colorful scarf for a pop of color. My hair was done in nice, loose curls, and my makeup was neutral and pretty minimal. After many freak outs about how I couldn’t do this and how it was now really real, I drove the few blocks to the restaurant where we’d meet up.

It’s safe to say that lunch was pretty terrible. Without going into huge detail…we met up and were quickly seated. We had what I’m assuming is normal conversation about why I joined the site and why I needed the money, which is fine. But then I quickly got confused when he started telling me what to look for in a SD. Some of the things that I should be looking for according to him includes: a married man or even a married man with kids is even better, and I should avoid a recent retiree. His reasonings? Because a recent retiree will want to spend all this time with me and want to know what I’m doing at all times, while a married man with kids will only want to meet up only a few times a week and then otherwise will be preoccupied with him wife and kids. Excuse me, but I’m pretty damn sure that I can decide what I was in a SD myself! It was only then that I saw the very distinct gold wedding band on his ring finger. The fact that he didn’t even try to hide the fact that he was married and even talked about his wife and kids with me was just appalling. If that’s not enough, then let me tell you that he even ordered for me. Now I know that in many fancy and swanky restaurants this is acceptable, but this place, while it was nice, was not nice enough to warrant that type of behavior. Bleh. I got a caesar salad and a half order of tortellini, which was all very delicious, though I wasn’t able to finish it because he finished his food first and kept looking over at me. Okay real cool, Coach. 

Lunch lasted for a half an hour on the dot (basically) and then he paid and we went downstairs to leave. The real kicker of the whole experience is when we were standing by the valet desk so I could pay. Coach instructed me to shake his hand and with that handshake he slipped me some money like some sort of drug deal or like I’m a hooker/prostitute!  It get’s even better because he just left after that with not another word. So little ole’ me looked at the money in my hand…expecting a nice amount and found myself with twenty-five dollars. You’re kidding me, right? I used that money to pay for my valet ($12) and then the tip ($2), which left me with eleven dollars. My understanding in the e-mail was that he’d pay for my lunch, valet, and then a small gift…not a small gift that I had to use for my valet. Bullshit. I then had to go buy some tampons, which I thought I’d use my ‘gift’ on, so now I’m left with three bucks. I don’t think that expecting more than twenty-five dollars as a small gift is some unreasonable expectation…especially from someone who “deals with rich people’s money” for a living.

It’s safe to say that this guy is not for me, nor am I for him. He obviously thinks that I’m some cheap girl who doesn’t know what she’s doing. Yes, I’m new to this whole thing, but I’m not going to just accept anything. I have standards and I know what I want and not just money wise… Though my presence is worth much more that twenty-five dollars. My search continues for the right sugar daddy and after experiencing my first ‘date’ with a pot SD, I feel a bit more confident and ready for my search to continue. I now know to get more business casual clothes that I can wear to nicer restaurants so I don’t have to fret about what to wear the night before. I just hope that my next experience isn’t as bad as this one. We shall definitely see, though!

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