Man/Boy #41, Not Your Sugar Mamma
I’m not sure what’s been happening lately, but all of a sudden there are a bunch of youngsters asking me out on dates. Currently, there are emails from three men under age thirty in my inbox on OkCupid. Can I call them men? Should I call them men? I don’t know. What is going on? Is there a MILF challenge trending on Twitter or something? Are they all ganging up to bag an older woman this month? Where is this sudden interest in me coming from? I don’t know. I’m completely confused. Men my own age don’t seem to be interested in me, but suddenly young boys my sons’ ages are.
You’re probably thinking, “What’s the problem? You go girl,” but dating men significantly younger than me has always been a challenge. It’s quite simple. I always start thinking about what my sons would think if I brought home a date who could be their brother. Granted, I have never asked them how this would make them feel. I just think they would think it was weird and wonder what the fuck I’m doing.
Just as I so often wonder what the fuck I’m doing.
So, what’s a…um…girl…to do?
Well, I made a date with one of the youngsters; that’s what. What the hell? You only live once, right?
Man #41 contacted me through OkCupid, “Hi! You are very beautiful! Can we get together to see if we have a connection? We should do coffee, a movie, happy hour, or something fun together. I’m a massage therapist…You can call\txt me any time…When are you free to get together? Hope your having a great day!”
Oh dear, another massage therapist. Ignoring the fact that he doesn’t know how to use you’re in a sentence and that his message sounded completely canned, do I dare?
He was cute, and I needed a date. At this point, I don’t have anything to lose. A while back when I passed up an opportunity for sex with a much younger man, I got chided for not taking the boy up on his offer, so I decided this time I would go for it and at least agree to a date.
We met at Sonrisa. (I know, again with the Mexican food.) He wanted to meet at 10 p.m., but I told him that was too late. Could we meet at 9 p.m.? Grandma’s gotta get in bed by eleven on a weeknight.
I arrived first and received a text from him that he was running late. This seemed like a passive-aggressive way to get the meeting time he wanted, but I made myself comfortable in the bar. I ordered a margarita and started slowly noshing on the complimentary chips and salsa. Before long, Man/Boy #41 arrived, and I was immediately uncomfortable. He looked younger in real life than he had in his profile picture. I wondered if he was even legal. What does one do in this situation? Should I ask for his ID?
Luckily, the waiter did this when he took his drink order.
Whew! At least he was 21. The waiter looked at Man/Boy #41 and then looked at me. I wondered what he was thinking. The waiter looked like he was my age. I’m sure he was wondering what I was doing with this youngster.
There were so many things wrong with this date I don’t even know where to begin. First, Man/Boy #41 had atrocious manners. He was very grabby with the chips, grabbing full handfuls at a time and chewing with his mouth full and talking while he ate them. He was also very talkative, telling me all about his job, how bad it sucked, and about how his mother died, leaving him with a house he couldn’t afford. He talked a lot about not having any money, and I got the sense he was looking for someone to help him.
I’ll admit; on one hand, I felt sorry for him. He seemed very young, lost, and in a very tough spot, but on the other hand, the whole scenario made me very uncomfortable. First of all, I’m done rescuing men. I have no patience for it anymore. It’s a thankless job, and I expect any man I’m with to have his shit together. Second, Man/Boy #41′s bad manners, the way he talked, rather loudly I might add, and the way he ate the chips made him seem like a twelve-year-old. It didn’t help that the waiter kept looking at us like he was trying to figure out what was going on. I couldn’t help but think that I’ve raised my sons to have much better manners than this. In a similar situation…God forbid…my sons could probably hold their own on a date with a woman in her mid-forties, but Man/Boy #41 could not. The thought, “I’ve raised three sons, and I’m not raising another one,” went through my mind.
Then he started talking about how he was a massage therapist, and he could give me a massage if I wanted one. Really? Again with the massages? I just need to stop here for a second and ask a question.
Are women really falling for this massage bullshit? They must be, or it wouldn’t be such a popular ploy. Can I just say? If I want a massage, cheap as I am, I will pay for a professional massage. I don’t want a massage from a man who is just trying to get in my pants. During a massage, I like to relax. I can’t relax if I have to worry that in mid massage I’ll suddenly find a finger in my cooch.
“Oops, I don’t know how that got there.” Really? There’s nothing I hate more than having my intelligence insulted. Do men honestly think this is a good way to ask for sex? Like women don’t see through the massage tactic? Or is it just me with my superior intelligence who gets this? Do other women simply say, “oh, a massage sounds nice,” and then wonder why there’s a hard-on in their ear halfway through the massage?
I doubt it.
No thank you. I’m not interested in a “massage.”
As soon as my margarita was finished, I asked for the check, paid my portion, and stood up to leave. Sugar Baby Wannabe suddenly stood up too and blocked me in the booth under the guise of trying to give me a goodbye “hug.”
Oh for fuck’s sake! This was IN the restaurant!
“Back up,” I said, “I need to get out.”
He moved and then insisted on walking me to my car, which was actually parked very close to the front door of the restaurant. I had been lucky in scoring “rock star parking.” Our waiter and another man from the kitchen were also outside smoking, so we again received weird looks from the waiter. This time, however, I was glad he was there.
When I got to my car, Man/Boy #41 was suddenly all hands again. It was like he had tentacles. In an instant there was a hand on my breast and he was trying to pull me in for a kiss. I pushed him away with some “wax on, wax off” arm blocks, and got in my car. Most of my dates end pretty calmly, but at 5-foot 10-inches tall and 240 pounds I am not afraid to knock somebody’s fucking block off if I have to. Plus, I’ll play dirty. I WILL fight like a girl, which means a man’s groin, instep, and eyeballs are all fair game.
What part of, “No, I don’t want a massage,” did he not understand?
The next day I received a text message. It read, “Do you think we could get together for a massage and sex? I would really like to eat you too. The worst thing that can happen is you will get an awesome massage and some awesome orgasms.
”
Seriously. I can’t make this shit up.
“No. I don’t think so,” I said.
“Plz. Just once. I would love to give you at least a massage. I’m a master at necks, backs, shoulders, arms, legs, feet and everything else. U would love it….
…No charge either.
Will you plz reconsider?”
“No.”
Man #40, The Music Man
Dating continues although much more infrequently than before. I know I said I was going to take a break, but online dating is a little like a treadmill. Once you start the thing it’s hard to get off unless you bring it to a full stop. So, although traumatized by my date with Man #39, when I received an invitation to join Man #40 for a drink, I went. What can I say? I grew up in Montana, and when a horse bucks you off, you get right back on.
I believe the failure of my date with Man #40 is all mine. I wasn’t very present. However, I don’t know if it mattered that I was present or not. He didn’t seem particularly present either. This was truly one of those dates that was so boring, it’s difficult to write about it. What I wouldn’t give right now for a man asking me to put a finger up his ass! NOT! No, believe me; I just want a normal date, but you have to admit the crazies make for better blog fodder.
Anyway, about Man #40…I had seen his profile on OkCupid. He seemed intelligent and wasn’t bad looking. He was also a musician, and you know how I love my musicians. It was one of those magical, OkCupid moments when both individuals, browsing the internet from their separate locations, mutually rate each other four or five stars. The next thing you know, an automatically generated email arrives in your inbox announcing that you have chosen each other. It’s so romantic.
So, I get an email from Man #40.
“Hi, got a message that you chose me. Not sure what that means, but anyway, I like your profile and photos. Would you like to meet?”
I responded, “Well, that message means I rated your profile 4 out of 5 stars. (I rarely give out fives.) I liked your profile for your love of music, your height, and your photos. I play piano and love to sing. I would definitely like to meet.”
And there you have it. We very quickly moved on to making plans for a date.
We met at Sonrisa, a Mexican restaurant at the University Village. Always trying to save money, I suggested we meet for the late night happy hour, which started at 9 p.m. I happen to know their sangria is pretty good. Man #40 asked if we could make it earlier, like 8 p.m. and I was fine with that. An hour later he changed it to 8:30 p.m.
Even better.
Man #40 was already seated in the bar when I arrived, and I chose to sit next to him on the booth instead of sitting across from him. I don’t know if this seemed weird or not, but I don’t like having my back to the rest of the restaurant. The tables in the bar at Sonrisa are high, and the extra height makes me feel really vulnerable when my back is to everyone. I wasn’t trying to be forward; I was just trying to be comfortable. It wasn’t like I sat down next to him and started rubbing his thigh or anything. I just sat down next to him. I have no idea whether my proximity on this first date made him uncomfortable or not, but it’s possible.
I took off my coat and made myself comfortable. I could tell that Man #40 was as tall as I had expected, but he seemed much thinner in real life than he did in his pictures. This made me feel self-conscious about my weight, and I found myself wishing I could shrink right there in my seat. I’m pretty sure my body language gave this away. I’m not sure how, but the feeling was so strong; I was certain he was disappointed by my size.
Overall, he wasn’t unpleasant, just sort of withdrawn. In a way, he was sort of like The Interrogator but with a less obvious, more laid back style. He was definitely asking me interview questions, but he was trying to be more conversational about it.
The reason I take responsibility for the failure of the date is, first, because of the choice to sit next to him instead of across from him. The second reason is because I waited to order my sangria until happy hour started at nine. I tried to play it cool for the first fifteen minutes and act like I wasn’t sure what I was going to order. I kept looking at the menu when all along I knew I was going to order the sangria. Then as the time grew closer to 9 p.m. I actually instructed the waiter to put my drink order in at the stroke of nine so I’d get the happy hour price.
I know. Tell me. I’m cheap.
Thinking back on it, I’m positive this made a bad impression. I’m like one of those cheap bastards who won’t even buy me coffee. He probably either thought I was totally broke, which I am right now, or worse, he thought I was trying to hint that he should pay for the date, which I was not. Yes, I appreciate it when a man offers to pay, and it does make a good impression, but I always show up with money to take care of my check. Always. I just don’t see the point in spending $7.50 when with a little patience I can spend $5.
It’s a sickness.
Then, in the course of my interview, he mentioned that he was thinking about buying a house on Lake Washington so he could have a boat. Most women hearing this would probably start assuming he has some money and try to snag him, but no, not me. I blew it by commenting that boats are expensive. I didn’t say it in some obnoxious, angry way. I simply stated it matter-of-factly. I’m pretty sure this is what put the nail in the coffin for my date.
Soon after, he said his jaw hurt and that he needed to go home and take some ibuprofen. It was the equivalent of “I need to go home and wash my cat.” He paid the check, walked me out to the parking lot, said goodbye, and I haven’t seen him since. It’s too bad really, because if we had gone out at a different time, like not right after my nightmare date with Man #39, I might have been my more entertaining, charismatic self. As it was, he got the “I’m so sick of dating I could hurl” version.
I don’t deserve to hear from him again.
And with that I leave you with a quote from comedian, Judy Tenuta,
“How many of you have ever started dating because you were too lazy to commit suicide?”













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