Ok, time to get real about dating. Whether it’s online dating, meeting men in the wild (shoutout to Girls Gotta Eat), or however else you meet people. Anyone who has dated in today’s world has more than likely experienced what I’m about to write about. Same shit, different toilet. Now please don’t get all butt hurt while reading this. But if you are butt hurt, then that is a good indicator that you fall into one of these categories.

Also note that I am not currently dating and have zero desire to after my last relationship. I can’t afford to be financially and emotionally drained ever again. I’m still paying for it (literally).

Reflecting back on my dating days, which now goes back over 2 years since I’ve been on a date, I have categorized the guys I dated. Mind you, some of the categories have more than one guy I could put in there, but I’m just going to include the highlight reel. The best of the best, if you will. I realize that women have their own categories, I don’t discriminate. But until I start dating women, I can’t speak to that. So here goes….

The Light Switch:

This is the real life psycho. They may come in different forms, but the end result is the same. During the first date, you’re genuinely scared for your own life. These guys seem normal when communicating with them online. I guess I’m lucky that I only really met one of these types. We had met online, and had been communicating for probably 2-3 weeks before actually meeting up. He lived the next state over, so we were going to meet up in the middle. He told me up front that he was going to rent a hotel room, as he didn’t want to drive all the way back home after the date (first red flag, though I guess if you can’t control your drinking, this would be the thing to do…so maybe this is 2 red flags). I never once said that I was going to sleep over in his hotel room, but apparently in his mind I had told him that. We never sexted or anything before the date, so there shouldn’t have been any sort of assumptions that we were going to sleep together. Admittedly, we did meet at the hotel and we were going to go out from there. This took place in Portsmouth, New Hampshire so we were going to hang out in downtown. Sounds like fun, right? I did not go up to his room, we simply met and then went out. We enjoyed a beer at a local brewery, talked, very casual. No sexual tension or anything, just good company. We were both German car enthusiasts, so we talked a lot about cars. He was very much in awe that a woman was into cars and knows what she’s talking about. Apparently that’s a huge turn on for guys. After we were done there, we went back to his room. Now obviously this was a bad choice on my part. I was no prude and wasn’t against sleeping with a guy on the first date. We’re both single, so why not if that’s what you want. I wasn’t sure that was going to happen, but I wasn’t necessarily opposed to it. We go up to his room and things get a little steamy, but didn’t go very far as he went to the bathroom so we started talking and I told him I had to go home at a decent hour. The “light switch” went from OFF to ON. All of a sudden, he turned. He turned into a fucking monster. He first started out like he was going to cry, saying he thought I was sleeping over with him. I told him I never said that, and I never would have (I never stay over anywhere because I had cats that needed to be fed…anyone that knows me, knows this is 100% accurate). Then he got very irritated after the tears. He actually left the room entirely…like stormed out saying he needed some air. At this point, I was picturing myself on an episode of fucking Dateline, as the woman who went out on a date and was murdered in a hotel room. So I’m literally at the door ready to run for my life, and he returns (apparently never left the hallway). He’s still pissed, and now it’s worse. I tell him I’ll give him half the money for the room rental, but that I was leaving NOW. He went down to the lobby with me, and I went to an ATM there and gave him money for half the room. Then I promptly left and holy shit was I surprised I made it out of there alive. The next day he texted me and apologized. I told him to fuck off. A few months later, on Thanksgiving, he texted me again wishing me a Happy Thanksgiving. I mean….really?? Then I blocked him.

The Roid Rager:

This guy would be an interesting person for a a psychologist to do a study on. What I’m about to tell you is very hard to believe, but I assure you, this is accurate and not an exaggeration. I came across this extremely hot guy online, and sent him a message thinking he would never reply because he was way out of my league in the looks department. To my surprise, he replied. He was a gym rat like me, had an amazing body. The kind of body you can tell even when they’re wearing clothes that they are what your wet dreams are made of. He actually seemed very down to earth, and we talked on the phone and texted for hours every day. It was mostly over night in the wee hours of the morning, as he worked 3rd shift in a machine shop. When he wasn’t working, he was working out, which was clearly obvious. After a couple of weeks, we had hit it off so well that we made plans for him to come up for the weekend (yes, I know). This was back in my bad decisions days. However, in my defense, he said he never slept with any woman on the first date. While that isn’t typical for any man (or woman) these days, I believed him. Here’s the part that I didn’t believe…..he also told me that he had NEVER masterbated in his life, and that he had only had sex with 2 women. Ever. He wasn’t religious or whatever, so I’m not sure what that was all about. I think he told me it was some spiritual thing. Was this a red flag? In hindsight, yes. But I was trying to keep an open mind. So he came up (he lived the next state over) one weekend. Nothing weird happened. He came over and we went out in the city, enjoying a meal at my favorite vegetarian restaurant and then went to a bar after. I remember thinking how safe I felt as we walked around the city that night, with his arm around me. For the first time, I felt good about someone. We went back to my house, watched some TV, and yes we had sex. It wasn’t until the sex that I realized he was telling the truth. He really had never masterbated and had barely ever had sex in his life. It was over and out in less than a minute. My girlfriend later named him “Gone in 60 seconds”. So now that I knew he was telling the truth, I actually felt even better about him. We spent the weekend together and had a great time. I felt normal for the first time in a long time. We made breakfast together, and things were going really well, albeit very fast. We even went to the gym and lifted weights together. He kissed me in the weight room, which made me feel a bit uncomfortable because I wasn’t used to PDA’s. The next week we spent talking and texting again for hours on the phone overnight.  He dropped the 3 words (I love you). I did not return those words, but he was ok with it. He came up and spent the next weekend with me. Things were still going really well. Then, the following week, he texted me in the middle of the night and said he “couldn’t do this anymore” and said he was moving to New Jersey. Obviously confused, I asked him what had happened. He then turned into a monster over text message. He had transitioned to The Light Switch guy. He started attacking me, saying I had slept with hundreds of people and that I had AIDS. Yes, he was TELLING ME THAT I HAD AIDS. Apparently you can test for that over the phone. First of all, we had never talked about my sexual history as he had never even asked. This literally came out of nowhere. So I gave him a piece of my mind and then quickly blocked his number so he couldn’t reply to any more texts or call me. Yes, I wanted to get the last word in. I mean, come on, this guy was fucking crazy! Months later, I went into my voicemail and noticed it said I had “blocked messages”. I had never seen this before. I went into that folder and saw that he had left me voicemails. Like multiple voicemails. He was telling me to call him, even getting irritated in some of the messages. I never called him back. Almost 2 years later, he sends me a friend request on Facebook and messaged me. He said he had moved back to New Hampshire from New Jersey. He was talking like nothing had ever happened. I didn’t accept his friend request, but did message him back and asked what the hell had happened. He said the reason that he attacked me was because he knew he was moving. I told him I was in a relationship (because I was), and then he never messaged me back. GOOD FUCKING RIDDANCE, YOU PSYCHO. The only thing I can think of is that he had legit roid rage. I don’t even know if he was on steroids, but what else could this kind of behavior be linked to?

The Stage 5 Clinger:

This is one we’ve ALL dealt with, am I right?? I had experiences with at least a few of these. The one that stands out is a guy I had one single date with. No sparks, no connection of any kind, and there was definitely no sex. This guy continued to text and call me after the date. Believe it or not, I’m actually a very nice person. So I continued to text him back for the next few days, but then the texts were like rapid fire from him. He wanted to text literally all fucking day. So I stopped texting right back, and then he got irritated, saying I was ignoring him and asking me what I was doing. For fucks sake, guy, I have a job. I have a life. I have shit to do. So at that point, I told him I didn’t want to continue this. I told him we didn’t have any sort of connection. He didn’t accept that. He asked, “well how would you know when we only had one date?” Ladies, please remember when dating, you don’t owe them any sort of explanation. You say no, you mean no. End of story. He finally gave up, but in his final words, he wanted to know what he did wrong, he wanted feedback. So I gave it to him. I told him he was way too clingy. Byeeeeeeee!

The Stalker:

These guys can sometimes seem perfectly normal, other times not so much. The guy that stands out here was my VERY FIRST DATE after I ended my 16 year relationship. I waited months before starting to date. So this was all new to me. I hadn’t been single since I was 17 and I was now 33 years old (at the time). I met this guy on, which I thought was a legit dating site. Turns out that all the dating sites (at that time) were really the same. I would later realize this as I joined other sites and saw all the same men on them. Didn’t matter if it was Tinder, Plenty of Fish, Farmers Only, or Christian Mingle. All the same guys. So my very first date was with a seemingly nice guy. He lived near by, so we decided to meet at a popular bar in town. We get there, and he had forgot his wallet. This has no bearing on the story, but it was kind of funny. He was going to go home to get it since he lived just a few minutes away, but I told him not to worry about it. It really was not a big deal to me. The date was blah. No connection or chemistry. He was a little socially awkward and kind of hard to look at. Not because he was ugly, he was just awkward. Not a big deal, it was just a first date. Nothing weird happened, and certainly no first date sex. I was still new to this dating thing and unsure about anything and everything. He continued to text me after that, but I told him I wasn’t really feeling it. I was and always will be, honest. So he actually started out as a Stage 5 Clinger but transitioned into The Stalker. Like the Stage 5 Clinger, he wouldn’t take no for an answer. He wanted to know why and wanted another date. I think I ended up having to block him after a while. Then, weeks later, I was at the gym lifting weights and saw him walk in shortly after I started my workout. I was in the gym 4 days a week back then, and had never seen him there. Then I remembered that I had told him that I go to that gym (remember, we live in the same city and very close to each other). I was very uncomfortable with this. Luckily for me, I was the female gym rat that was talkative with most of the regulars in the weight room. I made sure that he saw me talking to some of my guy friends there. Not that I couldn’t handle myself, but it’s always good to have a plan and to protect yourself. I continued to see him at the gym after that every so often, but never talked to him or even acknowledged him. After a while I stopped seeing him there. He messaged me through the dating app at some point but I ignored him. Hopefully he has since moved…out of the country. This would set the tone for the rest of my short lived online dating career.

The Lying Douche

Apparently I didn’t learn my lesson. I stumbled upon a guy online that (I thought at the time) was way out of my league in the looks department. Again, he clearly went to the gym all the time. His selfies were all the same….shirtless, flexing, making some really fucking annoying face (I think he started the duck lips fad that women embraced). But, in my defense, he also had photos of him with his daughter and also with his mother before she died of cancer. My mother died when I was 29, so this gave me a sense of a false connection. In his dating profile, he stated that he was “not looking for one night stands” as he “could get sex any time he wanted”. More red flags that I ignored. But the fact that he stated that, on top of the mother thing, made me think maybe this guy was serious. Now mind you, this was during my slut phase, but at the same time, I would have gotten into a relationship had the right person come along. I am not against sex on a first date, though now I would never do that (if I were dating). So the date went okay. Surprise! He talked about himself the entire time. I honestly felt like he was not into me at all, so I assumed that we would go our separate ways after the dinner. To my surprise, he asked if he could come back to my house since I lived right around the corner. So many memories at that damn bar. Anyways….so we hooked up. I was still naively thinking this guy might be serious. He never texted or called me after that night, even after I texted him saying that  if he wanted to go out again, I’d be down for that, but if not, that was fine too. Let’s be honest, that was probably the kind of text most guys would kill for. But I got no response. Ghosted. No loss. I moved on. This guy clearly has issues if he says he doesn’t do one night stands and then sleeps with this girl who is clearly new to dating. Months later, he messaged me on the dating app after I uploaded some new photos. He said he liked my hair long. I responded, “LOL”.

The Best Friend with Benefits (also, The Boomerang):

We’ve probably all had The Boomerang. Guys get bored after a while and decide to hit the same girls up, even after they’ve ghosted them. It’s the norm, sadly. But this guy was more than just The Boomerang. This was a guy I went out with very early in my adult dating career. I met him online, we went to the same gym, etc. Seemed okay, so we chatted and then went to the same bar I’ve been referring to in most of these stories. Hey, they have really good food and drinks, and it’s close to my house. For the record, I haven’t been to this bar in probably almost 2 years now. Actually I never go to bars anymore. I don’t even drink. Anyways….so this guy was very arrogant, very Republican, but also very charming in his own way. He had picked me up for the date, so when he dropped me off, we sat in his truck talking for a while. We both had had a lot to drink (which was the start to a very shitty pattern for me and this guy). I told him I didn’t think we had anything in common. He disagreed. He started listing all the things we had in common, which was all superficial shit. But again, I found him to be very charming. We hooked up that night. For some reason, it actually felt ok. Next thing I know, we’re hanging out all the time. To make a very long story short, we became best friends that were also fuck buddies. And if I’m being honest with myself, the sex was amazing. Definitely some of the best sex of my life. Friends with benefits is a dangerous thing. Best friends with benefits is suicide. I do NOT recommend it. I ended up having very strong feelings for this guy. We were lifting weights together, running errands together, taking the train down to Boston to go to Celtics games together, going to the beach together, I went to see him in Florida one winter when he was down there for a few months, we got into skydiving together, and the list goes on. But he had friend zoned me hardcore, but kept sleeping with me despite knowing I had strong feelings for him. It was a mess. Not a time in my life that I’m proud of. But at least I can admit that and talk about it. I was weak. It was the first real “relationship” type thing I had since being with the same partner for 16 years. I have so many stories to tell about this guy. While I realize that I should never have fallen for him, he treated me like a piece of shit after a while. He did and said things to me that would blow your mind. Yet he still kept sleeping with me. He still kept coming over to hang out. And I let him. This went off and on for a couple of years. Then something happened that broke the camels back for me. I ended our friendship and the fuck buddy status abruptly. I was heart broken, but I couldn’t do it anymore. Months later, he creeped back into my life at the gym. He would start conversations with me, despite me trying to avoid him. While I did start talking to him again at the gym, I didn’t sleep with him again. However, I was dating again and had met what I thought was a great guy who said all the right things. He was a skydiver, he was cute, and he made me feel really good about myself. We had been talking for months, and were about to start an actual relationship (or so I thought). Then one day, he told me he was going back to his ex girlfriend. Surprise! They hadn’t really ever officially broken up, I think they were just both cheating on each other and not talking about it. He had told me it was over with her. I was pretty mad. I’m not one for revenge of any kind, but for the first time in my life, I was ready for some form of revenge. To kill 2 birds with 1 stone, I called the Best Friends with Benefits guy. I literally drove to his place, fucked his brains out, then left. He wanted me to stay. I didn’t even say goodbye. I just walked out and went along my merry way. I can’t even tell you how GOOD that felt. That was a turning point for me. After that, I stopped dating all together until I met a decent guy. Another skydiver, but a decent guy. I thought things might work out with him, but he was young and the timing wasn’t right for him. We had a really good time together though, even spending a romantic long weekend in VT and I went to Thanksgiving at his parents house. But then he admittedly flaked out on me. I let it go, as I wasn’t fucking around anymore. I didn’t date again until I met this guy…..

The Con Artist:

This one is hands down the worst. He is what turned me off to men, and turned me off to people in general (more so than before). I’ll keep this one as short as possible, because honestly it still infuriates me and I’m still suffering the financial fallout. I met him at the drop zone where I was a skydiving student. He was a new pilot there. We hit it off quickly, as he is one of those guys that everyone loves. He knows how to play the nice guy part. He said “I love you” after just 2 weeks. I didn’t say it back for a month or two. I should never have said it back. But he told me all the things he thought I wanted to hear, even though I explicitly told him that I was not looking to change who he was as person. If we weren’t compatible, that was fine with me. I had been through a lot and been hurt, and I was perfectly happy being alone. Little did I know, he did the same shit to every woman he dated, but with me he hit the jackpot (literally). I don’t have kids, I own my own home, I have a good career, I make good money. The money part is what was missing with his previous girlfriends, as I would later find out. Some of the details are hindsight, some are red flags that I clearly ignored. I’ll admit that. While he was spending the shit money he was making as a skydiving pilot on drugs and alcohol, I was working my corporate job and paying for his medical bills, making his car payments that he had missed, paying the vet bills for his dog that was diagnosed with cancer, taking his dog to my vet for the diagnosis, taking his dog to the specialist to try and treat the cancer, and ultimately paid to have his dog put down. I loved that dog as if she was my own. He actually told me to keep her ashes, which I still have. He knows I took better care of her for the short time she was in my life than he ever did. We adopted Peach together. He promised me that he would get a good pilot job with decent pay and benefits after he spent the spring and summer flying skydivers in Moab, Utah. So he was gone for 6 months, only coming home to me for a couple of weeks here and there. Meanwhile, I was busting my ass at my job and now also had a rescue dog that we had adopted together. He made so many promises. He said he’d get a second job while out there to make some money to start paying me back. Nope. That didn’t happen. The money he made out there he spent on alcohol, weed, cocaine, shrooms, acid, you name it. To top it off, he was more than likely cheating on me. He lied to me and later admitted it, putting it back on me as if I was crazy and “made” him lie. This isn’t even the worst part. The worst part is that one night, when he was actually home, he kicked the shit out of Peach. I had flashbacks of my father kicking the shit out of my mother. I was stunned. I will never forgive myself for allowing a scumbag to manipulate me and to do that to MY dog. He acted the part really well, often crying and apologizing to me, but also constantly telling me I was paranoid and had jealousy issues. Really all I wanted was a boyfriend that had a decent job, was home most of the time, that could financially contribute, and that could help take care of the dog when I was working sometimes. Is that too much to ask? Well, that never happened. He broke up with me over the phone, while still out in Moab, after a year and a half “relationship”, and after taking thousands of my hard earned dollars with no intention of ever paying me back. He swore he’d pay me back though. I never believed him at that point, but I wasn’t going to let it go either. You see… can fuck with my heart and my emotions. But don’t ever fuck with my money or my dog. I hounded him for months for my money. He sent me 2 payments, totalling something like $350 or so. Out of $8000 that I had records for. He even took my skydiving helmet and wouldn’t ship it back to me. He finally paid me for it like 6 months later. He moved to an island in the Pacific Ocean, married some woman who needed a VISA maybe 3 months after breaking up with me, continued to tell me he was in love with me, even just 2 days before his wedding. This was, by far, the worst experience in my life. This guy ruined me in every way. And I let him. I haven’t dated anyone since, and that was almost a year and a half ago. I have no desire to date, no desire to even sleep with anyone. The Boomerang (BFF with Bene’s) even tried to worm his way back into my life, but I rejected him (more than once). I’ve decided that when/if I am to date ever again, it won’t be with men. Hey…..every woman is a little bit lesbian. I say that jokingly but I’ve always believed that. At this point in my life, I honestly don’t care. I just want decent human beings in my life, whether that be friends or partners. At the same time, I am more than happy being single. Every day life is hard when you’re doing everything yourself as a homeowner/pet mom to 3/career woman, but it’s much better than being with someone who disrespects you and treats you like dirt.

Needless to say, I’ve learned some HARD lessons. But I do take full responsibility for my own actions and for allowing men to take advantage of me. This is what happens when you’ve been in a relationship since you were a teenager and then all of a sudden need to experience all the things most people go through in their 20’s, except now you’re in your late 30’s. The best thing to come out of all of this is that I have my dog. The next best thing is that I have vowed to NEVER ever treat another human being the way I have been treated (not that I ever did).

At the end of the day, I can laugh at myself. Now my question to my single readers (female AND male) is….can you relate to any of this? If you’ve dated at all in the last decade or so, I’d bet my life you can relate.

I may be done with dating, but my animals aren’t. Mario is currently on Tinder, and Peach has a few boyfriends at daycare. Yoshi is a momma’s boy that no other woman can live up to.



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