I normally look for men to date who I feel are on the same footing as I in terms of age, education, and economic status. The only hiccup there is I haven’t found anyone I jive with enough to make it serious. Frustrated? You betcha. No problem; cue roommate:

Roommate: All these fucking guys are like little boys. Seriously, you need to date an older man. With money. If you’re going to be heart broken, at least be wined and dined first. 

Because she has some awesome power over me, and frankly, has a goddamn good point, I did as I was told and signed up on a match-making site where millionaires go to find a significant other. Mind you, I didn’t have the intention of being the next Anna Nicole Smith looking for a sugar daddy. I was just curious to see who else was out there and honestly, slightly desperate to find a new scene since what I’ve been doing obviously hasn’t been working out. To my surprise, the pool of men weren’t all that creepy or decrepit. Sure, the majority are in their 50s or later, but for the most part, they were all seemingly well-educated, refined, and stable. Could this be the goldmine that I’ve been overlooking???!


Pretty much immediately, I received a few responses to my profile. A few propositioned me for sex in turn for “gifts”. Um, no thanks. I’m not much for whoring myself. I rather give it away for free in exchange for some saved dignity. That’s just how I prefer to roll, OK? After sorting through tons of gray hair and wrinkled faces, I ended up responding to good ol’ Richard. He didn’t come off as looking for a sugar baby but more of searching for a real companion. For this I was grateful because I was getting fed up with the pervs who wanted to use their monthly prescription of Viagra on me. I thought,”What the heck! He’s as good a start as any other!” Let the communication commence.

After several long emails of introduction and questions, I found that Richard was a hot shot 52 yr old lawyer from Beverly Hills who was fit and had all his hair, divorced for 14 years, father of an 18 yr old daughter, and for a hobby, was an avid pilot. I’d have to say, our “courting” was rather different. He asked questions that were more substantial than what I was used to from younger guys (e.g. So what are your plans for this weekend? Are your friends as hot as you? Got any more pics to share?). He seemed to really want to get to know me and respected that I wasn’t just the run of the mill gold digger. Yay!

Like all relationships that start on the internet, there will always be a time when they want to meet in person. At first he wanted to fly me there, but I refused since I didn’t want to feel as if I’m accepting a gift of sorts. He then offered to fly his private jet to come see me. Alright, sure. You come see me, so I won’t feel as if I owe you anything. Deal.

I’m not going to lie. I felt super awkward about this. Did I seriously think something romantic can happen with someone who was 25 years my senior? Granted he didn’t look like a grandpa per se, but the age disparity wasn’t exactly understated either. Before I had the chance to talk myself out of this, my roommate gave me the push I needed to go through with meeting him in person. Go and have fun, she said. There’s nothing to lose, she said. Uh-huh…

I picked up good ol’ Richard from the airport, and I chose to go downtown and get some ice cream. Nothing like a crowded public place to stay safe, got it ladies?! As we were sitting and talking, he reached over to hold my hand. Dude, the first thing that crossed my mind was, “Eek! No! What will people think?! Stop invading my personal space!” Yeah, obviously not a good sign if I wanted this to go somewhere, right? Hindsight…

Spending a couple of hours for a getting-to-know-you chat, we decided to have dinner at a local Thai restaurant. Conversation went well, and I was actually loosening up and enjoying his company. We discussed a myriad of intellectually stimulating subjects until a young couple walked through the door. He looks at them and says to me, “They’re obviously fucking.” I nearly choked on my vegetarian pad thai noodles. Oy, can we say inappropriate and disgusting? I quipped that they could be platonic friends. He refused to believe that and iterated, “No, he’s definitely fucking the hell out of her.” Double oy! So what if they are? Why should you give two shits about that, you deprived old geezer? I think it was at this point I began to fixate on his gray hair, deep set wrinkles, and the loose skin that slightly bunched at his neck. *shivers* Thankfully, we only stayed several more uncomfortable minutes before he paid for the meal with his black Amex. I suppose I was to be impressed. I wasn’t.

Things got a little more unnerving after I took him back to his hotel. Again, in hindsight, I should have dropped his ass at the curb, but I walked him up to his room. I sat in the single chair as to not give him any ideas. That’s when shit really got disturbing.

Wait for it… wait for it…

He pulled out a piece of paper and said, “I brought this in case we decided to get romantic. It’s my test results to let you know I’m clean.” OMFG. A) How damn presumptuous and B) FUCKING EW! Alrighty, time to bounce. Peace out, homie.


The next afternoon, I picked him up to take him back to his airport. Yes, I’m pretty damn courteous to go back aren’t I? I think he got the hint that this was going nowhere because he didn’t mention anything inappropriate on our drive. He just told me he was disappointed I didn’t stay for a few drinks at the bar with him. Boo-freaking-hoo. Shouldn’t have turned all creepilicious on me, you old Dick. Thank you for spending a day and several grand to gas up your jet to teach me that I need to be way more into money to settle for a horny, old fogie- no matter how educated or “refined”.

Never again. I was curious, so I tried it out, but I was left feeling ill, so now I’m done.

Moral of the story #1: No matter the age, most males are horny, disgusting bastards. However, this is permissible if you find him attractive. Otherwise, it’s just fucking infuriating.

Moral of the story #2: If you’re not a gold digger, you most likely won’t last one date with someone who has saggy balls. You’ll lose your stomach contents.


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