Date 4

I was perusing through Tinder on the train (ignoring every nosy fucker trying to look at my screen), and i came across this profile for this 26 year old teacher. He was pretty cute (well my type….dark hair, tall, glasses). And he had a master’s degree. For some reason stuff that like turns me on. Im a total sapiosexual. So i swiped right and immediately it was a match. Mazel Tov. Anywhoo, his name was Mike and he was a history teacher for a private school. I chatted with him for awhile and it was his birthday. I had another date so at about 8 o’clock the other guy cancelled. I asked Mike if he wanted to come over. He said he was supposed to have cake with the family for his birthday but he was going to come over and tell his parents he’ll have it another night (which was red flag #1….the guy totally dissed his parents!). But i gave him my address (and i do my due diligence. I used to be an investigator so I am great at finding out about people and I actually have GBI clearance so I can have a few more tools at my disposal. Plus, he was way too dorky to be murdery. (Btw, i tend to like dorky guys). So he came over and right away there was chemistry. It didn’t even bother me that he rented his parent’s basement apartment (teachers don’t make a lot of money and NYC prices are insane). As soon as he walked in we started making out. I don’t usually do shit like that. But there was a definite connection. I didn’t expect much from this situation. We had sex and of course which was really good (the chemistry thing again) in my horribly awkward post-sex chat, i asked him how he felt about abortion. And how he felt about George Bush as a president. I was not expecting how conservative he was (though i should have guessed when one of his photos on tinder was a trip to Bibleland in Orlando with his family. Anyway  he said each fetus is entitled to due process and that he didn’t believe in abortion. (Also i not only get a birth control shot every 3 months but use condoms), I really don’t want something terminal like a kid. And he also started talking about how we should go traveling this summer when he’s off from school. I said i’ll think about it (and think about it means no fucking way…a) i like to travel by myself…its very important to my psyche) and b) im not going cavorting around the country with a guy i barely know. He eventually left. I didn’t hear from him for a couple days. And then when he finally called me (yes he called and not texted) he told me he was in love with me and wants to marry me. And i said hold on there. You don’t even know me. You don’t know anything about me. He’s like i can tell what type of person you are and i love you and i want to be your husband. So i said i don’t work like that A) you are too young and B) i dont want to get married.  Oh and in between this time i found out his parents are strict catholics. And i said you still live at home. And he said “oh i’ll move in with you”. And I’m like no thanks..I live in a studio and also I DONT WANT TO GET MARRIED! So every day I got pressure from the kid. He was calling me constantly and then all of a sudden for two weeks I didn’t hear from him. And then he texted me and said I love you, i want to marry you, we are going to have sex without condoms, and you are going to tell me you love me. And that clicked something really really angry inside me. I said don’t call me again. And then two days later i got a call from him saying he saw a therapist and he’s better now. And i said you don’t get better from one therapy appt. I said I’ve been going to therapy for almost 30 years and I’m still fucked up. And after like two more times texting me i blocked him from my social media, blocked his phone number and said to him if you ever come to my apartment every again, I’m calling the cops for you stalking me and also calling the school you work at,  because I don’t put up with that nonsense. My take away from that debacle was don’t date a 26 year old and be like only the 2nd person he’s had sex with. I haven’t heard from him. I hope he found a nice 20 something year old catholic girl he could boss around. And they can living happily together in his parents’ downstairs apt.

Date 3

The third person I dated was from Georgia and currently lived in NYC. He worked for the Department of Homeland Security. He couldn’t tell me exactly what he did. But clues helped me figure it out. We went out to dinner on a date. He liked really large breasted women, so I don’t think it mattered to him what type of personality I had. He didn’t really look at my face. His name was Ryan, btw. After our date he had to go to Switzerland on behalf of the DHS. I asked him to bring me some Swiss chocolate back. He got back two days later and came over (by this time we had been speaking regularly for a month). With Swiss chocolate in hand. We started talking and he reaches into his bag (he had to catch a flight after hanging out) and pulls out a Glock. I kid you not. I was like wtf?? Because he had top government security clearance (way more than what Jared Kushner has) he was allowed to bring it on the plane. I asked him to put it away. I’m not a fan of guns or guys I don’t know super well bringing guns into my apt. I knew he wasn’t gonna shoot me though. Why would he spend money on Swiss chocolate for me just for him to see it wasted? He also told me he had 5 different passports. We ordered in dinner and then for dessert had sex. He hung out for a little bit and I asked him where he stood politically. I think he said he leaned conservative. I’m TERRIBLE at the after sex talk. He then had to catch his flight. He got back a few days later. We met up again a few times and then like 3 weeks later told me he was being transferred to their Atlanta office. So that was the end of that. I didn’t lose much sleep over it. I’m not a fan of Southern accents. Or guys that just look at my boobs. Or guns. Or conservatives.

Date 2

So my friend from work decided to change my age range on my Tinder as well as swipe right on a ton of guys while i was getting coffee. Yes, we are still friends. It’s very hard to stay mad at him. But no, I will never let him touch my cell phone again. Anyway, he changed the age range from 18-28. I think I had 29-45 or something. I got like 5000 “super likes”. One of the people he swiped on I actually thought was cute. He was one of the “super likes” And he was 28 so near the cusp of the beginning of my age range. So i swiped back. A lot of swiping …so this acci-swipe was this guy named Adan. He was a photographer. We chatted for a little bit. His mom was British and his dad was Moroccan. We met for drinks near my apt. I make almost every guy shlep out to Queens. I think i feel safer in my ‘hood. After talking for awhile over drinks we came back to my place. I found out he was Muslim. And I am Jewish but that didn’t bother me. We made out for awhile and then he left. The next week he came over and we drank some wine and watched tv. And then slept together. And he was really good in bed. When we’re lying in bed after sex, I said to him “So….how do you feel about the Palestinian-Israeli conflict?” Because of course I’m the most ill-timed awkward person on the planet. I am NOT one for cutesy small talk. 😀 He actually said he doesn’t know why people are so mean to the Jews and every Jewish person he’s ever met has been really nice. He said after what the Jews went through they deserve Israel. That they fought a war and won. I was actually quite astounded. Then out of nowhere he  said my blow-jobs were “magical”. Which was also oddly-timed but a really nice compliment. And also made me forget about my post-coital current affairs question. He didn’t run after that conversation. We saw each other for like a month after that but I have A.D.D. when it comes to men and I get very bored quickly. So I told him i met someone and moved on. He kept texting me for awhile wanting to come over but I think he got the hint. Also, I hadn’t met anyone (well seriously…i was talking to a lot of guys), but I’m very passive-agressive and didn’t want to hurt his feelings. Plus, very few guys give that nice of a bj compliment. And they say chivalry is dead.

Date 1

Btw, my content will be pretty graphic and racy. I want to be as authentic and genuine about my dating so no holds barred. If you find material like this offensive, feel free to stop reading 🙂 I’m pretty liberal and open about my life. It’s just who I am. I’m not doing it for shock value or anything. Usually I don’t share everything with complete strangers, but I don’t plan on running for office. So what’s the worst that can happen?

Okay…so my first date after I moved to NYC. I was perusing Cougar Life, because well, I really like younger guys. I find they have less baggage and less ex-wives. I came across this profile of this guy named Jhon. And no I’m not protecting anyone’s name. Because well, eff that noise.

So I was talking to this Jhon guy, and he was like “when was the last time you had sex”? So i said about 3 years ago. Yes. I didn’t have sex for 3 years. THATS how much relationships have fucked me up. The trust issues didn’t help. So he’s like “can I come over”? I figured I should get back into the sex pool. Not to be confused with sesspool. Though they kind of are the same thing. I asked him where he lived. And he said NJ, but the town was like in the middle of NJ. Not even Newark or Hoboken. So about an hour and 15 minute drive. I said sure. Which is probably not the most prudent or safe thing to do, but he had a FB profile, so I figured he’s not a serial killer (also im totally being sarcastic). But i just had a feeling he was okay. He actually friended me on FB before he came over.

While he was driving I noticed he unfriended me. So I texted him and said “we arent facebook friends anymore” and he’s like “i dont know what happened”?? But i knew exactly what happened because I am very smart and know how people think. That this was purely a booty call, which I am also not used to. I mean I’ve had sex with guys I wasn’t in relationships with, but we actually saw each other regularly.So i was thinking I’ll let this slide (twss?). Anyway, he got to my apartment and was way better looking than his photo. I was wearing a tank top and pajama bottoms and he asked if he could touch my breasts. So i was like sure. And then he said he wanted to take a shower and that i should jerk him off in the shower. So I am pretty easy going. I said why not. He got out of the shower and we got into bed. We had sex (it was probably a 6 out of 10). Not too creative but a nice looking penis. And then like 10 minutes later he was out the door. I never heard from him again. But at least my dry spell was broken.


Thanks for checking out my blog. Im a 45 year old female that works in Technology and lives in NYC. 6 years ago I was in an 11 year relationship. After that amount of time I realized I missed dating. And our relationship had kind of run its course. So we broke up. We are actually really good friends. He lives in Las Vegas with our dog (she likes him better even though I spoil her more…and I was the one that actually wanted the dog!). BUT I was with him from age 28, so my entire 30s were with one man. When I turned 40 I felt it I had to make up for lost time. I didn’t remember what dating was like. My entire twenties I was also in relationship after relationship. I felt I needed to stay single for awhile. Three years ago I moved to NYC for a job opportunity and I figured I’ll start dating again ( I was not ready to date for 2 1/2 years before that and I still have HUGE trust issues). Basically the point of this blog is to give you insight into my dating experiences, some interesting stories, and the realization that even though I’m middle-aged, I still have NO idea what I’m doing. I’ve got to be the worst dater ever. I always do or say the wrong thing. So hopefully you can learn from my mistakes and have a laugh along the way.

Good company in a journey makes the way seem shorter. — Izaak Walton