Tag Archives: dating after thirty

Benn G., my sweet 27 year old

10 Sep

bennMind you I’m 35 now, so I have no business messing with this boy. BUT Benn G was the really cute 27 year old that I went on all these NYC dates with. Central Park picnic, baking cookies, mini golf on the pier, Happy hours, Street meat. All so fun. I really enjoyed this guys company and by date 6 all of my girlfriends were pressuring me to give up some goods. At this point I had been back to his apartment twice for a heavier make out sessions, but stopped them each time. I did touch his dick once and it was surprisingly large and perfect. I’m pretty easy to please (physically) unlike most girls so size has never really mattered much to me with guys. Still a nice surprise considering he was on the slender side, muscular, but a little tall and lanky.

I got weirded out by this guys somewhat freak side. He carried cufflinks keys on his keychain and would always say how hot it is to put them on a girl during sex. I would joke…please romance me more, then change the topic. So weird! He was really good looking so I tolerated it.

Anyway date 7 rolls around and I invite him over to my place for dinner. He had earlier said he would bring wine. I slave over the kitchen and spend about $100 on groceries making skirt steak and crabcakes from scratch for him with roasted potatoes on the side. I made a bowl of fruit for desert. He comes over empty handed, so I say I don’t think so go across the street and buy us some wine. I knew that night was going to either be great or awful and I at least wanted to know he bought me something. I’m pretty sure I had shaved and prepped all areas full on thinking I was going to have sex with this guys after dinner. I knew beforehand I was going to have some kind of conversation with him if he was seeing anyone else because that’s obviously a no go for me.

I’m a gamer and have an original nintendo and xbox at my place, so we play some old school mario and then decide to get busy. We outgrow the couch and move to my bedroom. I ask him in so many ways if he is seeing anyone and matter of factly he says “oh that’s one thing I’m absolutely not wiling to do. Not going to be exclusive with anyone” I think I was stunned and disgusted at the same time, but kissed him and said well I absolutely cannot sleep with you then. Not going to lie it got a little awkward. I’m straddling him with my dress over my hips and thinking how the fuck do I get off him without being incredibly rude. We actually kissed a few more times because my vag and brain were having a ferocious hateful debate that my brain ultimately won.

I kinda rolled off him and told him I really liked him and I’ll probably make out with him again, but I can’t do this. He laughed and said he really liked me too. He left my apartment shortly after that. I was sad and disappointed, but what was I thinking with a 27 year old anyway?!

I had no desire to text or follow up with him and genuinely felt like a dodged a bullet yet again, but my vag was still really f’ing pissed. Weeks if not a month goes by. I distract myself with Matt S., the British Rugby player and a slew of other usless guys in the meantime.

I invite him and a bunch of people to a group happy hour and he surprises me and shows up.  A lot of people showed up and I had a new guy there I was loosely interested in. Same flirtation started we took turns buying rounds for eachother and then he ferociously made out with me as soon as we walked out of the bar. He was totally trying to kiss my boobs in the cab and I was like slow down. It was HOT though! He does this really weird thing with his tongue though that I hate. Ick!

Anyway we arrive at the next spot a guy friends bday party at Empire hotel. Was kinda a ghetto weird crowd, but good music, so whatever. Benn buys me a drink which I love because he’s so cheap. He’s acting all coupley with me then these girls walk by, not cute mind you, but probably closer to his age, say 30. He’s like hey nice seeing you guys you are so and so right. He proceeds to totally ditch me the rest of the night, which I hardly noticed because I was talking to a bunch of other people at the bday party, but after about an hour I’m like wtf. He walks by me and apologizes saying the girl might be helping him get a job. I don’t really believe it, but I don’t really care either because again he’s 27 and this is stupid. He’s just really cute. Ugh fml!

So I’ve scheduled yet another happy hour again tomorrow that he’s responded that he “maybe” going to on facebook. Maybe he’ll surprise me again and show up and we’ll ferociously make out again. Maybe not. After hanging with all these cheating guys he seems like a breath of fresh air that was at least honest with me. Is this what it’s come down to ladies of NYC? The cheating guys or the guys that just want no strings attached sex? I’m not buying either option, but it makes me sad that as a woman I have no one to be with physically. Makes me kinda want to cry though. I want nothing more than to have a man in my life, but they don’t exist here. Just stupid boy players that are even in their 40s. I feel like eating a box of chocolate chip cookies for dinner. In fact…yes I will do that and then run 8 miles at the gym. I haven’t yet gotten to Matt S. and Leo G which all just happened last week and this week. The cookie thing will make more sense then. I’ll save that for this weekend. As for now I’m officially playing Leo…hee, hee…fucker :).

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Dating Guys that Live in Your Building

30 Jul

Ok, so I’m not sure if I posted this before,  but last year I sorta hooked up (PG) with a guy that lives in my building on the 6th Floor. This guy isn’t the most attractive guy in the world, but he was and is super smart. If guys that can’t write a proper sentence or type in all caps piss me off to no-end, a guy that is super smart will definitely be a turn on. He went to one of the best undergrad schools in the country and also got a business degree from the same school. So by no means is he an idiot…academically speaking.

The 6th floor guy from last year was actually the first guy in NYC that took me out on a proper date since before him I was in a 7 year relationship and then a 5 year relationship. I met the 7 year relationship guy in college, so there was no dinning or taking out. I met the 5 year guy about 5 months after splitting from the 7 year guy and just needed company, so I was willing to accept anything in terms of dating venues and guys for that matter. He took me out for a slice of pizza in Little Italy for our first date and he didn’t even eat, so you can’t really call it a formal date. He leeched on to me for a long 5 years after that, but I was the idiot that let it happen.

I’ll add a formal post on what went down with this guy last year. In short he’s a mess! But he likes to creep back in my life whenever we see each other in the lobby. He’s even gone so far to tell me in the street that he’s had dreams about me saving him. He’s told me he wants to give me babies, BUT…he’s a drunk, has had episodes of serious drug abuse, gambles too often, and loses jobs frequently. Who knows how we pays his massive mortgage, but not my problem. Right?

I’m a chatty patty and I love my doormen and the building staff, so I’m always in the lobby talking to these guys. On Friday night I see the 6th floor guy I hooked up with last year and he’s covered in bruises. Not surprising because he’s a mess, but he asks me to go out with him to a neighborhood spot. He’s dangerous, so I’m not really interested, but at the same time, I’m really worried about him and his self destructive ways. It’s like the dysfunction draws me in, which is messed up, so I stay further away.

I’m still hanging in the lobby when 20 mins later this other guy in my building walks by that lives on the 21st floor.  I’ve always thought this guy looked so cute in a suit and tie and he tells me I look gorgeous. I’m like what the hell?!? This guy never says more than 5 words to me and now he thinks I’m gorgeous? He walks back in the building and I realize he is way too talkative as he’s chatting me and the doormen up. He’s definitely been drinking. Whatever…if the liquid courage got you what you need to talk to me….keep talking.

So he goes back up to his apartment and I walk my pups. I see him on the street 5 mins later and he invites me out. I like doing random, yet safe things so I say yes. He walks with me and my pups since he also has a dog and says he’ll wait for me. Before we get back to our building he runs into 2 girls he used to work with and is like verbally vomiting on these two girls about how he got laid off/fired. I’m like great another loser guy! He just kept rambling to these girls and I felt awkward and embarrassed for him. This should have been a warning sign, but I’m an idiot and we go out to LES around 2am.

He’s all like I know a promoter at Hotel Chantelle  and we can get right in. I’m like ok whatever. Clearly his promoter was taking a while and I also knew someone there promoting named Lisa and texted her and we got right in bouncing the huge line. Once we are in we finally get to interact a little and I can’t tell if this guy is just really drunk or just weird. No wonder he never spoke before. It was like I said “up”, he would say “down”. I would try to say a joke and he would take serious offense to it. It was like we were speaking different languages. I was really turned off by this, but I like to understand things so I stayed. Plus he bought me two drinks and was very protective and polite, which was nice. He did try grabbing and holding my hand multiple times, which I thought was annoying. I’m thinking “I don’t know you…get off me”. Again, all these guys are so grabby. I have a tiny waist and curvy hips, so guys are always touching that and it get’s annoying. Don’t touch my hand or my waist until I give you the green light. At least wait till the 2nd date. This wasn’t even a date!

So all of the sudden we were with 3 other people and we were trying to remember who sang a song together. There were girls laughing and just being drunk, flirty, and silly and 21st floor guy get’s all pissed and says they were “clowning him”. This guy clearly has self esteem issues or something. Before I know it he’s saying he’s got to go and just decides for us that we are leaving. I have to quickly say my goodbyes and I turn around and he’s gone. Luckily I got a glimpse of him out the door talking to car service.

I run out the door and I ask him if he’s leaving me…shit we can share cab fare you know. He’s like “No, I thought you would like it if I got us a cab”. There were like none around, so he “negotiates” paying $20 to go from LES to Midtown East. Fucking idiot! He also wanted to “take care” of our driver and he had no cash. So I ended up paying the $20 and he gave him a $10 tip. What an idiot!

So we finally get home to our shared building after only being gone for an hour. Weird! I want to end the night, but this is where it gets tricky. We get in the elevator and I press both our floors. He’s acting awkward and he’s like “don’t you still want to hang out?” I’m thinking no I don’t want to hook up with you just leave me alone, but he follows me off my elevator and I have to rush back to my apartment to avoid my dogs barking and waking up neighbors. Fuck! So now this guy is in my apartment. And to make matters worse he’s acting like he wants to move in. WTF!?! He eventually kisses me, but it was a really wet kiss that included him licking from half way down my chin to then sucking on my bottom lip. What the hell is wrong with guys? I definitely had to wipe my face off after that kiss…GROSS! Please God why do you put all the weirdos in my path? And why are they all such bad kissers. Almost every guy I’ve kissed in my 30s has been a disgusting kisser. Is this why they are all still single? Ugh!

He says he wants to take me out to wine and dinner on the following night which would have been Saturday, but I had a bday party to go to at Fontana bar. I invite him to come and he’s like yeah we can go get a drink and then go there. I’m like cool and don’t worry about anything else. I just want him out of my apartment.

Saturday comes and we text in the morning and he is sweet. I think I’m sweet back, but I don’t like texting all day with no purpose at the same time. He says he’s going to take a nap and I respond “Talk later”. He responds “What?” and again I feel like I’m explaining or defending myself. WTF?!? I know guys sometimes have fragile egos, but this was extreme.

Hours go by and around 8:30 he tells me he’s sick and is staying in. What a fucking nut job!

It turned out I had a blast on Saturday with like 8 of my friends and met up with another 20 people at the bday party. The company was great, but I wouldn’t recommend Fontana bar. It’s too divey, definitely not a Saturday night spot.

In fact, one of the guys there was hitting on me all night and tried to even crash in my loft, but I wasn’t having it. What is it going to take to have a normal, attractive, compatible guy walk into my life? Sigh!

At any rate, the guy I dated from last year on the 6th floor that same night sent me a text around 4:25am responding to my text the day earlier. The only thing I texted was that I worry about him.  He responded a day later “Haha, go fuck urself. U don’t care and I don’t deserve it” then immediately called me to ask if we could “cuddle”. Insanity!

He apologized for that whacked out text on Sunday and asked me to go see the Batman movie. I made an excuse. Ugh! What’s wrong with guys. These are supposedly the smart high earning guys too. Are all us girls screwed?