Age ain’t nothin but a number

After the night I hooked up with that 22 year old waiter we agreed to be friends. I really didn’t hear from him again. I couldn’t really blame him, I probably wouldn’t have called someone who got wasted on a Wednesday and banged me in my mom’s basement again either. We texted here and there for a couple days and then he disappeared. I don’t keep numbers I don’t use in my phone, so I eventually just deleted his number and kinda forgot about the whole thing.

Tuesday night I got a text from an unfamiliar number so I asked who it was. Then I noticed I had an Instagram message from the waiter so I had kinda already figured out who it was before he even responded. He wanted to know if I wanted to meet for drinks. I was planning to make it an early night but decided instead that meeting up with him was probably gonna be a lot more exciting than going to bed at 10pm so I went and met him with him.

The bar was empty except for us and some drunk middle-aged people. He tried teaching me about fantasy football and it seemed like he was trying really hard to impress me. I was starting to feel like I was on a date I didn’t Intend to be on and not like I was hanging out with a friend that I drunkenly accidentally hooked up with. Eventually, I mentioned that my sister might wanna meet up with us when she got out of work but he said that he would rather the two of us just hang out and talk.

When the check came he paid the bill and wouldn’t let me give him more than 10$ towards it, that was about the point that my suspicion was confirmed I was on a date and we weren’t just two friends hanging out and having a couple drinks. I have found myself accidentally on more dates that I didn’t realize were dates than most people I know have been on on purpose.

The bar was closing so I started looking for another bar to head to but he said he would rather go back to his place because no one as home and we could have a couple more drinks there. I am like 30 and have no business being in anyone’s mom’s basement, but I didn’t have much else going on so I figured why not.

I had remembered the sex not being very good, but I had hoped that maybe it was because I was really drunk that first time. contrary to popular belief, most drunk sex isn’t good. Sadly it wasn’t the vodka that made it bad, It was actually worse than I remembered, such a waste because this kid literally has one of the biggest Johnson’s I’ve ever seen. He isn’t a big dude and this thing is just like a freaking monster, but as we all know its not about the size of the boat its the motion of the ocean and that seemed to be lost on him. It was super quick and at one point he just kind of laid on top of me not really moving but had the audacity to ask me if I was gonna cum. It took everything I had in me not to say “yeah dude I’m coming to my senses right now and getting the hell outta here”, instead I went with something along the lines of “yeah probably after I go home”. I have got to block his number or something, this is just bad, not to mention it can never go anywhere because he is WAY to young for me. Though I could probably take the mature route and just talk to him about it.

I know I sound like a dick for counting him out because of his age and some bad sex. I know sex is teachable but it’s not even about that. For one he is just to nice for me to tell him its not good like I really don’t wanna hurt his feelings. But also he is so smart and a really talented artist, like he could build a computer from nothing and his room is full of all this really great artwork yet he still thinks the coolest thing about him is the fact that he sells weed. I found myself needing to stop myself from momming him and letting him know that most of those people were only his friend because they were getting something from him and that in the not so distant future everyone was going to be able to buy weed at the gas station so he should probably find a new side hustle. Plus I’ve said it before and I’ll say it again, nothing is less impressive to me than a guy that can only talk about how much weed he smokes, granted he’s not as obnoxous about it as other guys I’ve gone out with but its obnoxious enough to be a turn off for me.

I haven’t really heard from him much since I’ve been back from vacation and I am kinda hoping it’ll stay that way. I would love to be able to be friends with him because he’s a good person and he is nice to spend time with, but he definitely isn’t the right person for me. I don’t have a future as a cougar that’s for sure.

 

Airplanes

Last weekend, I went on a date with a guy I met on Tinder. It was fine, but he was a shitty tipper. If you know me, you know that is a huge deal breaker for me. If someone else is buying my drinks I probably shouldn’t be so critical, but having worked in the industry it’s just something I really notice. Aside from that, he was a nice guy, with a decent job, who came from a nice family. I wasn’t sure we really clicked, but I almost always feel like that after a date. I’m starting to wonder if I’m the real problem.

Before the date was over, we agreed to go out again on Saturday. We were going to meet for brunch at this restaurant I had been dying to try since I moved to the city.

He texted me a lot and always said good morning. It was something I really enjoy so I was thinking the tipping thing would be teachable. Before our brunch date on Thursday night, he asked me if I wanted to meet for drinks again. I said yes. By the time I was free it was kind of late and he was understandably tired. I offered to just see him on Saturday, but he invited me to his place instead. I sort of knew it was a booty call. I figured we were both adults and he was upfront about what he was really looking for a little second date schtokus wouldn’t hurt. Plus, I wasn’t sure about him anyways so I might as well get laid.

The sex was great, think like the episode of SATC when Charlotte is dating that guy who makes her blackout when he’s going down on her, great. It’s so rare that I hook up with someone and think ‘damn can’t wait to do that again’. I found myself in a sex haze, the kind that makes you think I can put up with someone’s bullshit because the sex is so great. You really start to wonder if the things you didn’t like about them were valid, or if you are just making shit up because your trying to protect yourself from getting hurt again.

The next day he started acting weird. That was when I realized he was one of those guys. The ones who lie to girls about what they are looking for to just get laid. (There goes my sex haze). Honestly, I didn’t think that was a thing guys had to do anymore, now that Tinder is a thing. But hey- I guess if this guy’s willing to spend $100 on a date to get laid and never talk to me again…he’s probably not the type of person I want to spend my time with.

He claimed he was sleeping all day. Part of me really wanted to believe that, but, I really could sense the bullshit from a mile away.  I wasn’t surprised when he texted me an hour before we were supposed to meet on Saturday. He bailed because he “wasn’t feeling good.” I knew he was full of shit. But on the off chance he wasn’t lying, I told him I hoped he felt better and let him know when I was free next. He never responded. I had already decided that I was going to get brunch whether he was with me or not.

I decided a long time ago I wasn’t going to do the things I wanted to do just because I didn’t have someone to do them with. Brunch waits for no man so I put my good butt yoga pants on and headed out.

It was BYOB. I sat at the bar and drank a bottle of champagne by myself. Halfway through my meal, two girls sat down next to me and commented how ‘ballsy’ it was for me to be brunching alone with my bottle of champagne. They were sisters, in town for a wedding, both living in different parts of the country. I gave them some things to do around town while they were here. I mentioned I wanted to visit Texas (where they grew up) but had been putting it off because I wasn’t sure what I would do once I was there. They made me a list of things to do and where to stay if I ever decided to go.

My time with those girls (and a bottle of champagne) got me thinking. I realized a long time ago, that I had put off a lot of things in my life. All because I was doing what I thought I was supposed to do and not the things I wanted to do. So I decided to book a flight. Flights were cheap. It was actually the second trip I’d booked this week. I guess you could say my life has become sort of  drinking game. Instead of drinking every time someone says the word ‘ass’ …..you book a flight every time your disappointed by a man.

I guess you could say that right now I’m on the verge of some sort of Eat Pray Love type of journey. Except for me its mostly just eating…. and drinking. Probably not good for my liver or the size of my ass but hopefully it’ll be good for my soul …..or whatever. At the very least I will get to see what else is out there, and maybe make a decision on where and how I want to restart my life.

Brush your shoulders off

I’m not sure if this is the best or the worst thing about me, but I always push things as far as I possibly can. So last week when I got yet another message from a guy asking me if he could be my sugar daddy I responded the same way I responded to the other 750 guys who send me messages asking me to pay me for sex, I gave him my venmo and told him to put his money where his mouth was and send me something to prove he was serious.

I never expect anyone to actually send me money. I figured he would do what every other guy has done and disappear or tell me to go fuck myself. Instead, this guy paid me $25. It wasn’t a ton of money but it was the most money anyone has ever given me for no reason and it was enough to pay my bar tab that night so I was thrilled. Totally confused, but thrilled.

After he sent me the money he started asking me for pictures. Obviously, I’m not into that and even if I was my nudes are worth way more than $25 so there was no chance I was gonna send him anything. He wanted to know what he was going to get for his money, I let him know that he was getting an opportunity to “interview for the sugar daddy position”. I figured that was going to be the last time I ever heard from him but I guess that was a satisfying enough response because he asked me if I wanted to get drinks the following week.

I probably shouldn’t have agreed to meet him, but to be honest, I wasn’t totally sure if he was actually that much of a creep or if he didn’t just send me the money to call my bluff.  If that was the case I was kinda into it, but I figured at the very least if we actually did meet for drinks it was probably going to be hilariously weird, and its not like I would’ve had much else to do, and it was a public place so really the worst thing that was gonna happen was that he was actually a total creep.

We were supposed to meet for drinks Monday night. I asked him if we were going to discuss my allowance on our date. I was mostly kidding but apparently, he wasn’t because homeboy actually started discussing how much money he was willing to give me every week and what he was going to expect from me in return.

It was super weird especially since what he wanted were really vanilla things that most women do for free, and he was a good looking guy so there really was no reason he should even NEED to pay for sex. I guess it’s just his kink, to each their own I guess. He started asking me to send him pictures, and once again I decided to see how far I could push things, so I told him I was going to need some sort of deposit on the sugar daddy arrangement in order to send him anything.

I seriously thought he was finally going to tell me to go fuck myself or something but instead, he started negotiating a price for me to send him pictures of my boobs. I told him I wanted $250, at this point, I just wanted to see how much I could get out of him before he unmatched me. I didn’t think he would actually seriously negotiate a price for a picture of my boobs, but we wound up settling on $150 for a picture on snapchat with no face and I wanted the money first because ” this wasn’t mamas first rodeo” (it totally was my first rodeo).

I basically shit my pants when he actually added me on snapchat and then venmoed me the full $150. He drove a hard bargain but one thing he missed during the negotiation process was the clause that said they had to be naked boobs. He must’ve been super surprised when he opened his snap chat the next day and found a picture of my boobs, completely covered by my t-shirt.

Probably not what he was expecting, but sometimes, when you play stupid games you win stupid prizes and I became $175 richer for doing absolutely nothing.  Naturally, I haven’t heard from him since and as expected he blew off our date  which isn’t really much of a tragedy, his venmo featured his full first and last name, which I looked up on facebook along with the city he told me lived in which is where I found all the pictures of his girlfriend. So not only is he a creep trying to pay girls money for sex he’s also cheating on someone so, to be honest maybe I was a little bit of a scumbag taking money from him but in the end, he did kind of get what he deserved.

Champagne Problems

Last night, I matched with a guy on Tinder who seemed really great. We talked for a while, and eventually he invited me to dinner. At that point, I was already in the process of cooking and couldn’t really stop and change my plans, so I asked him if he would be available to meet for drinks in a couple hours instead. He said yes, then added that he didn’t drink but he really liked ginger-ale. Cue internal screaming.

Lately, I’ve been encountering a lot of men who say they don’t drink, and every time I hear it I instantly lose interest. I know this makes me sound like a raging alcoholic, but hear me out on this.

Alcohol is not a deciding factor in my life, I really don’t drink that much compared to other people in my age group, but when I see myself in a relationship, I see myself with someone who will go out with me on a Friday night and have a few drinks in a beer garden, or at a bar. It’s something I could never really do in my previous relationships. If we’re being honest, getting either of my ex’s to even spend time with me was like pulling teeth.

If I am going to have a relationship with someone, I don’t want it to be another relationship where I have to do everything alone, or one where I get criticized by my partner for going out and having a couple drinks with friends. I literally spent 10 years in relationships where I had to go to events by myself because I had partners who didn’t drink. When I was able to convince them to go somewhere with me, most of the time they would sit and pout and be rude, to both to me and anybody with us. It was embarrassing, and I really don’t want to have to deal with a lifetime of similar situations.

My other reservation is like- what do you do on a first date then? I generally try to avoid going for a meal on the first date, opting for drinks instead. Drinks are fast and easy, 20 minutes tops, and there’s no pressure. And if things aren’t going well you can leave after one drink, rather than staying for an entire meal, which can be upwards of an hour or more. Also, if things aren’t going well during the meal, it honestly feels a lot like being held hostage.

I like the option of being in-and-out if I need to, and it’s also cheaper. If we wind up splitting the bill or I pay, I don’t end up spending a bunch of money when I didn’t have a good time. If he pays, I won’t feel so bad about not wanting to see him again.

Recently, my dating app conversations usually go like this- they ask if I want to get together, I suggest we meet for a drink, they respond with something along the lines of “I don’t drink but we can smoke a blunt if you want”, I tell them I don’t smoke, and plans are never made.

I don’t have an issue with weed, but all my last ex ever did was smoke weed to the point where we couldn’t do anything that didn’t revolve around it. He was constantly spending all of his money on it, to the point that I wound up paying for almost everything when we lived together. I know that in most cases this is not the norm. I also know that the real reason he was like that wasn’t because he smoked weed, but because he literally didn’t give a shit about me or anything I cared about.

Still, I can’t shake the internal cringe I feel every time a guy suggests smoking a blunt as a date. I know people are fully capable of smoking and not being a dick about it, but something about offering to take me on a “blunt cruise” as a first date is a real turn off.

Surprisingly, that’s not what happened this time around. He didn’t offer to “smoke me up on a blunt”, he just accepted my bull shit excuse and my promise that we could meet for an appetizer later in the week. He even continued the conversation. That was when I started wondering if I was just being a giant asshole in not giving this seemingly great guy a chance, just because he didn’t drink.

I am such a proponent of not letting the bullshit from your past relationships affect your present life but here I was doing exactly the thing I tell so many people not to do. So, when he gave me one last chance to meet him for appetizers that night, I impulsively decided I should just meet up with him. It wouldn’t kill me right? Plus, the meal I cooked sucked anyway.

We met for appetizers. He wound up being pretty great.

I still have my reservations about dating someone who doesn’t drink, but its only been one date. Also, if he can not be a dick about the fact that he doesn’t drink and I do, I think he and I could have a lot of fun together. I guess we will see.

 

Bad Romance

Have you ever had sex and it was so bad that you felt like you owed your vagina an apology when it was finally over? That was me Sunday night.  I have for the most part sworn off one night stands and fuck buddies, but I have been really in my feels lately trying to figure out what I’m doing with my life and just generally disappointed by dating in general so after dinner and a few drinks with friends when the opportunity for a hook up came about I took it.

I had recently changed my tinder settings to include men ages 21-35 which I think makes me a cougar but I’m not sure. I don’t really know why I decided to do it but I think it was a combination of me being sick getting weirdly timed poorly lit selfies from middle-aged men and I maybe had gone on one too many dates with men over 30 who for the most part haven’t learned that you cant hurt everyone who tries to care about you just because someone did it to you. On day one I matched with some 22-year-old kid who wasn’t far away from me. He was pretty adamant that he was going to somehow manage to rock my world. I guess I did kind of set him up for failure when he told me how women have told him how “good he was with his hands and tongue” to which I responded, “yeah no one is ever going to tell you it was terrible but thanks for playing”.

When he was messaging me earlier in the day I said it was a possibility. I knew I had been super in my feels and probably needed to get some and I also knew I was gonna have a few drinks so I figured I would leave it open-ended so that if I was feeling like I get some cradle robbing strange I would have the opportunity to. Around the 6th vodka soda, I mentioned that I might be into it. Next thing I knew he was in the car on the way to Worcester and at that point I felt bad about backing out so I just gave him my address.

So he comes over and he’s a nice enough kid. We start getting things going and he can’t uh… rise to the occasion. He starts losing his mind and literally SLAPS HIS OWN DICK. I’m just sitting there like woah- we are in my own house- how can I get out of this. I thought he was going to cry. He finally ends his limpdick induced breakdown and we start hooking up and suddenly I wasn’t sure if I had a vagina or a construction site down there because he was like a god damn jackhammer.  The whole ordeal only lasted about 20 minutes but damn it was the longest 20 minutes of my life. It was one of those experiences that made me wish I had never moved my emergency hammer away from next to my bed.

Chasing Waterfalls

Being the last single friend in your friend group is difficult for many reasons, the most difficult being that you have so many well-intending friends and their spouses are constantly trying to set you up with their terrible single friends. Sure not every set up has been terrible and I know that my friends just want to see me happy and in a healthy relationship for a change but damn some of the most ridiculous things that have ever happened to me on a date have happened because I let my friends set me up. Blind dates may have worked for Meghan Markle but they sure as shit never worked for me.

Initially, when I moved to this city I made a lot of new friends. That heard has since considerably thinned but within that group was a guy that everyone wanted to set me up with. He was “a bit weird but needed someone like me to get him out of his shell” and “would definitely treat me better than anyone else I had ever dated”. At first, I was firmly against this because he was weird and not necessarily in a good way but after a lot of convincing, I finally agreed to hang out with him.

I had some friends over for dinner and they insisted on inviting him. I decided to go with it because if I at least gave him a chance it would shut everyone up, it wasn’t gonna kill me to spend a little time with him, and who knows- maybe we would’ve hit it off. We had pasta and I felt super awkward and got incredibly drunk because vodka is the most logical way to deal with any awkward situations. My friend went to sleep in my guest room which left me alone with this guy they were trying to set me up with.

My drunk alter ego has a bad habit of sleeping with guys I don’t want to see again the first time I meet them. So the next thing I knew I was in bed with this guy who was telling me he was into some “really freaky shit”. I had heard this before but usually, the freakiest shit most guys can come up with is like wanting anal, I figured it was that so I dragged it out of him (and for the record that NEVER would have happened). The next thing I knew he was asking me to pee ON him.

I thought that was like a fake porn thing that people weren’t really into but here I was with some guy I wasn’t even into asking me to pee on him. I know everyone has things they like but somehow I feel like that is not a thing you ask a girl the first time you go out with her, especially if you know you are going to have to see her again. In most situations, I would have run as fast and far away as I possibly could but we were in my house and there was only so much I could say at that point because I knew I was going to have to see him pretty often.

What made it even worse was that he would not leave. He stayed the entire night which I don’t even allow a guy to do unless I am seriously dating him and the next morning he kept trying to get me to take a shower with him. Like NO JUST LEAVE JESUS CHRIST IT IS WEDNESDAY MORNING AND I NEED TO GO TO WORK. I felt bad but like there was no way that was ever happening.

I learned a couple of valuable lessons that day. First- don’t ever sleep with someone you’re going to have to see on a regular basis if you aren’t sure they aren’t into some weird shit. Second- always keep a hammer next to your bed….. just in case.

Harlot

So every once in a while I go on what I think is the worst date I have ever been on. First there was the guy who called me a racist because of the town I grew up in (which by the way is not a racist town at all…??) and practically yelled at me because it was our second date and I wasn’t gonna bang him, Then there was the lion- who told me he wouldn’t tolerate coffee consumption because “thats an addiction”, and lastly there was the guy who never got his drivers license because of 9/11. They were not bad guys just really weird. But my date from last Thursday definitely won the gold medal when it comes to the dating Olympics.

He had been messaging me on and off for a couple weeks. He’d start a conversation and then disappear for a week or two, come back and pick up where he left off. I mentioned I was newish to the city and he offered to show me around, I figured it couldn’t hurt to see some new bars. I had been sort of sick to my stomach all day when he asked me if I wanted to get a drink with him. Despite the fact that I wasn’t feeling that great I agreed to go out with him. I figured I could be miserable at home by myself or I could go out and grab a drink- it wasn’t like I was going to feel any better whether I stayed at home or not.

We agreed to meet at 7- I even texted him at 630 to confirm that we were meeting at 7, so I was more than a little annoyed when he texted me at 7:05 to tell me he was 8 minutes away. I considered leaving, but I had put on real pants and makeup and I already had a drink so I figured the least he could do was pay for my drink if he was going to be almost 20 minutes late.

I assumed he was probably coming from work which would have been a reasonable excuse, I get held up at work all the time- I don’t usually wait until 5 minutes after I was supposed to be there to let someone know, but I consider myself to be an extra considerate person. I found out this wasn’t the case when he informed me that he was on disability and hadn’t had a job since 2004. I try hard to not be judgmental about people on disability but dude- you could have at least shown up to the date on time since you and I both know you weren’t at work. Things are going ok- they weren’t terrible, but he was alot older than his profile said he was, he hadn’t worked in a very long time, had no long or short term goals, and he had a criminal record. He just wasn’t the type of person I saw  a future with, but I was already there so I figured I would just see this one through.

At about the same point that I realized there was not gonna be a second date he tells me hes going to “go outside and bum some cigarettes”.  My 36 year old date then drags me outside in the cold to bum cigarettes from people smoking behind the bar. Everyone has their vices, I get it- but at 36 years old you should be able to support your own habits. At this point it becomes clear that I am probably paying for my own drinks. He asks me if I want to head to a different bar he wants to show me. I say sure, to be honest I don’t know why I didn’t end the date at this point- I still wasn’t feeling well, and I wasn’t having a particularly good time, but I’m a really nice person and he was having a good time so we paid our separate tabs and head to the next bar.

We get to the other bar and it turns out hes a regular there. He starts sharing stories with the other patrons, and I am feeling super out of place. We stay for an hour or so and then he tells me to grab the tab. I end up paying the tab for the last two drinks. So to recap- he’s bumming cigarettes, I paid for my own drinks at the first bar, and both of our drinks at the second bar.

I really should have gone home after that. But if were being honest I really needed to get laid, and I’m having minor surgery at the end of the month that will put me out of sexual commission for a few weeks so I figure I would seize the opportunity to get it in with someone I didn’t worry about impressing to much and didn’t plan to ever talk to again. He takes me back to his apartment on the other side of the city and we start getting down to business when all of a sudden my stomach ache gets worse. I start feeling really sick and tell him that I wasn’t feeling well and that I need to leave. He tells me its late and I should stay the night plus “he wants to keep banging”. I again reiterate that I am not feeling well and am going home. He disappears into the bathroom and I hear the shower running. So at this point I figure its pretty clear to him that I am not feeling well and I am leaving. I pack up my stuff put on my clothes and leave. 10 minutes later I get a barrage of angry texts about how I “just dipped” “wtf is wrong with you” and my personal favorite “your tits aren’t that great I was interested in your personality but that just went down the toilet good fn luck maybe you should try not going home with people the first night if your gonna be a whore and leave”. Like DUDE first of all calm down, your dick game was mediocre at best. Second of all did you want me to projectile vomit all over your studio apartment? What did he expect I was gonna do? “Be a whore” and move in as opposed to be a whore and leave? He didn’t even wait for a response he blocked my number and unmatched me faster than he turned that bar tab over for me to pay.

I mean I guess in hindsight I probably should have just thrown up in his bed. Like hey dude I’m having a bad night and now so are you- but I really thought leaving was the appropriate way to deal with it, and I really don’t know how much more clear I could have been. Not that I really care what an almost 40 year old who cant even pay for his own drinks thinks of me, it was more that I just couldn’t believe that this grown ass man was throwing a literal temper tantrum via text messages. I guess the moral of this story is if he’s lame in the streets hes gonna be lame in the sheets and hes probably going to call you a whore.

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