Tag: dating fails

Listen, Judge Judy…

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After dating for fiftyleven years, I find myself now reaching breaking points. I’ll put myself out there so much and open up and be completely honest. I don’t know how to be any other way really. I’ve gone on so many dates and dated people that were mediocre or straight up brutally awful but I still keep trying because I’m…hopeful? Curious? Stupid? A masochist? Who knows? Lately I’m feeling exhausted and skeptical and cautious and fucking over it.

“Love”. That’s the end goal right? Or is it? Is that what I want? Or do I need attention and entertainment? I’m content with the humor that comes from dating. I enjoy discovering the weird in everyone. It’s intriguing to me. Until it’s not. This year I had dates with 4 men in June and became exhausted. Until October. I went on dates with 5 more men in the fall. They broke me. I’m done. As I’ve discussed with many of my fellow single friends, we’ve reached our breaking point. This shit is NOT. WORTH. IT. Seriously…it’s so not worth it.

I’m perfectly capable of fucking up my own life. I’ve also met plenty of people who can assist me in that. I know that from years of experience. I’ve got my life together though. If I ever get in a relationship again, I want a companion who also has their shit in order. Someone on the same page. I need someone who has also lived and died a few times. Someone who has experienced all sorts of weird and fucked up stuff and survived to tell their tales. But also someone who can be completely transparent in communication. No secrets. No lies. No judgement and no bullshit. Someone who doesn’t have their mattress on the floor and someone who has hobbies and interests and education. Someone well-traveled and compassionate. Someone who makes me laugh but knows that I’m funnier than he is. Maybe also someone ridiculously good-looking. Tall, rich, ripped like Jesus and hung like a horse. I am NOT asking for too much!

I could also be completely happy staying single forever and occasionally taking loverrrs. (MeYOW!) I’ve never felt the need or strong desire to get married or have kids. I love my life as it is. I love doing whatever I want, with whomever I want. I don’t have to answer to anyone. I love kids but I love dogs and drinking wine so much more. I was MADE to be an auntie. The wild, eccentric one who is a little tipsy or maybe hungover. I always thought I’d be like Elizabeth Taylor or Zsa Zsa Gabor. A glamazon-type woman who marries and divorces as quickly as the wind changes course. Fuck that though. Sometimes I don’t feel like brushing my hair and marriage and divorce were not fun. 0 stars. 0 out of 10. Would not recommend. I did it once and I’m scarred for life.

Is “love” with a “soulmate” the real end goal here? Do we all believe in that? Or is procreating really everyone’s goal? This all sounds a bit outdated to me. I learned that during the pandemic and the insanity of Trump’s presidency and this insane election and the crazy divide in our country, along with the income inequality and racial injustice, climate change and THOUSANDS of other fucked up issues, I have less and less of a desire to “achieve” these things.

I also feel like many of my friends who are married or married with kids are unhappy more than they are happy. They resent their spouses. They resent their children. They resent their in-laws. They resent their single friends. They miss their freedom. They’re bored with the monotony of their life. I don’t want to feel that way.

I think they actually resent themselves for the decisions they have made. The grass is always greener… Some of their single friends are jealous of their lives though. A ton of them are. They crave the stable life and consistency. They desire the ring and 2.5 children. They want the financial security that often comes with having a partner.

These “taken” friends though. These “happily married with children” friends. These “friends” are also the first to spew their advice and judgment on their single friends. Listen here, Tiffany, the last person I want relationship advice from is the person who just chugged a full bottle of tequila while calling her husband a prick repeatedly, whining about not ever having sex, and feeling unheard and unappreciated, crying about being in love with her ex, being sick of digging Cheerios out of the couch cushions, wishing she had more time to herself and hating her post-baby body. I didn’t make your life decisions for you, so stop trying to make mine for me.

Bottom line: Stop taking advice you don’t want and stop giving advice that is not wanted. We all have our history which has led us on our path or journey to our future. You didn’t grow up like me and I didn’t grow up like you. Just because you wouldn’t make the same decisions someone else made, doesn’t mean they’re wrong. Just because we don’t all have the same goals in life, doesn’t mean any of them are wrong. I’ve said no to many marriage proposals, stood up in countless weddings, left a marriage and said goodbye after an engagement. I’ve also stayed too long in relationships and situationships. I’m more critical of myself and my decisions than you ever could be. It’s not your place to judge, just as it’s not my place to judge you. I’ll walk my path and you walk yours and I hope both are happy in the end.

Hoppin’ off my soapbox now to get back on my bullshit!!

The Painfully Boring guy

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At this point I can’t count the number of dates I’ve been on this year. It got to the point where I stopped calling them dates all together. This was business. These were meetings. I kept my two drink maximum rule and managed at one point to meet 7 guys in 4 days. You think I’d be burned out. This had become a second full-time job. I wasn’t burned out yet though. I loved meeting all these weirdos. Some were cute, fun or nice but there was nothing there between us. They’d make good friends but they weren’t boyfriend-material. One of these guys was Cary.

As soon as I walked in and saw him I knew this was the first and last time we’d meet. Cary was a tricky little bastard. All of his pictures were from when he still had hair. He now carefully places the few bits of fuzz he has left in a way that, from a distance, makes it look like he still has thick and luxurious locks. Up close though it just looks like a tiny, thin black veil floating about an inch and a half above his scalp. It’s hairsprayed to hell and that shit ain’t movin’. As a hairdresser, I could fix this mess. I could help him out here. I don’t want to though. I don’t want to have to fix or change things about someone. Been there, done that. Never again.

Cary and I ordered a beer and got this meeting started. I’m asking all the questions to get the weirdness out of Cary and I’m getting nothing. All he does is smile and nod at everything I say and basically repeats my answers to questions that I ask him. He’s eager to please and say all the right things but I don’t think he’s ever had one original thought or idea in his life. One of my hobbies is painting so all of a sudden Cary LOOOOVES painting. When was the last time Cary painted? When he was in elementary school. I enjoy running and doing yoga and lifting weights. I can tell by looking at Cary he’s never worked out a day in is life but I ask anyway. Cary LOOOOVES working out too but claims he just doesn’t have the time lately.  I have two dogs and wish I could have 48 more. Cary LOOOOVES dogs too. I asked Cary if he had any pets. He does not and never has.

I also could not stand sitting there listening to him go through the entire beer list with the server to figure out what he wanted to drink. The entire time he mispronounced every fucking one of them and in the end he just told her to pick one for him. He’s like a little spineless jellyfish. He’s the kind of guy who would probably make a great husband one day if you want to constantly boss someone around who will do anything you say with a smile on their face. He’d be like a slave and a puppy and husband in one.

I could feel my eyes getting heavy as he was literally boring me to sleep. I’ve never sucked down two Daisy Cutters that fast in my life.  We walked out together, waited for our Lyft or Uber drivers, hugged and left. The next day I got a message from him on the app. He wants to “take our relationship to the next level”. I obviously did not want that. After that night I learned how much I appreciated people with opinions and hobbies and backbones. Poor Cary. I’d tear him apart. There’s no way he could handle someone like me. I could see him with a girl who thoroughly enjoys tea and practices needlepoint on a Saturday night or has a collection of stamps. She will dress like a librarian in the 80’s and not wear makeup. She will wear orthopedic shoes because she thinks they’re cute, not because she actually needs them. She’ll be obsessed with cats and have a cat-themed apartment. She’ll even have cat salt and pepper shakers. Their idea of a good time will be having a staring contest for hours. They’ll hold hands but they won’t have sex because neither of them ever have done it and they’re both too timid to initiate it. Holy shit! Sorry…I can just envision her perfectly. Basically what he needs is NOT me.

How do I kindly tell Cary that our relationship will stay on this level and not progress any further? I could ignore him and ghost him like most people do but I have respect for other people and would never do something that cruel. I could describe to him (in detail) who I think his perfect match is but I’m not sure he’d be receptive to me offering to help find her for him. I opted to just tell him I’m not interested. I thought about how to say it for a couple hours and then I responded. I told him I had fun the night before (ok, I lied a little) and although I think he’d be a good friend, I wasn’t interested in dating him. Then I held my breath and waited to see what would happen next. Was he going to have an epic meltdown on me? Was he going to cuss me out and tell me what a bitch I am? Nope. Cary actually thanked me. Despite the fact that he said he was disappointed, he wanted to thank me for actually responding to him to tell him how I felt. We wished each other luck finding someone relationship-worthy and unmatched. That was not nearly as painful as I expected and it was far more enjoyable than our entire date the night before! I really hope Cary finds someone to boss him around soon.

The Underemployed One

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It’s Sunday morning and I’m doing the 30-something’s Walk-of-Shame from my Saturday night guy’s place, which is Ubering home, hung over, while texting my friends about the previous night. That’s when I get a Bumble message from a guy asking if I was interested in getting some brunch. Yes. Yes, yes, yes. The answer is always YES to brunch. We agree to meet at a brunch place my friend manages, as I’ve repeatedly promised to come check her new spot out and fail every time. I raced home to take care of the dogs and get cleaned up. When I’m almost there he texts to let me know there is an hour wait so he’s at the restaurant next door having a drink. It’s 11am. He’s drinking. We’re off to a good start.

I get there with my perfectly polished ponytail, giant sunglasses and pale yellow sundress that my friend Nikki just gave me, attempting my best (somewhat hung over, ‘I hope I don’t still smell like sex’) Audrey Hepburn look. I recognize him immediately from checking out his photos, even though it was clear his photos were quite old and he was a bit heftier than he was when they were taken. We hug and I order champagne; my drink for summer 2017. Hey, I’m celebrating being alive this summer! We get down to chatting and I notice he’s wearing very expensive, trendy, yet classic clothing but his eyes were glazed over and bloodshot. His shirt was unbuttoned a bit too far and his hair was wild. I asked how his night was and he told me he went to Cuvee, an upscale nightclub, the night before with friends. Despite having delayed responses to any of my questions, he responded and asked questions as well so I wasn’t leading the entire conversation. Something still seemed off about him but I guessed it was just his hang over.

On his profile he said he was a beverage director at a nice hotel. I asked him how he liked that job and he tells me he was fired from that place a year ago. Why the fuck does it still say it on your profile then, guy!? So I asked what he does now and why he was fired. He goes on to say he was fired for being “kind of an asshole and a drug addict”. LOVELY! He said he talked down to his staff and he didn’t realize other people didn’t use cocaine the same way he did. He basically did it all day and all night, in front of his coworkers and bosses, and was shocked that it was an issue when they brought it up to him and dismissed him from his role in the company. Now he claims to be underemployed, as he works as a bartender two nights a week at two different bars. This cocaine habit now explains his delayed responses and blood-shot eyes. This dude is still awake from partying last night!

Cocaine

I knew I wasn’t attracted to him but we were here already and I was hungry. After almost an hour, I asked if he wanted to check on our table status next door at my friend’s brunch restaurant. He then tells me he never put our names in so we had just been sitting around the whole time waiting for nothing. This guy needs an adult. I run over, climb over 30 hungry people who are sitting around, waiting for their names to be called. I pull the dick move of name-dropping at the host stand and hug my friend Sarah after the hostesses get her attention. She was running around like a mad woman but told me there are seats that will be available at the bar. I run over to tell the underemployed guy to drag him over before he orders another cocktail.

When I came back and told him, he then lets me know that he has no cards and no cash so if I could cover everything today, he could Venmo me or get me next time. I’m getting fucking PLAYED right now!! This broke-ass scammer got me! I ask why he wanted to invite me to brunch if he has no money but he assures me he has some in the bank, he just left his debit card at the nightclub last night. You’re a 30-something year old man who only has one card to his name and you leave it somewhere and invite a girl out?? What’s WRONG with you? Where did you go wrong in life? Shit, where did I go wrong in life if these are the guys I’m meeting!? I pay and we go next door, order food and a drink and continue on this “date”. I talked to my friend and the bartender now more than I talked to this guy. He picked at a salad and slowly sipped a bloody Mary while I crushed some eggs and veggies and two champagne cocktails.

We decide it’s time to go since I hate him and he has to actually go to one of his jobs soon. My friend kindly discounts half of our bill, I pay again and then decide to run to the restroom before we walk out. Before I go, he tells me to close my eyes and hold out my hand. I fear something bad will happen but I look around and realize we are elbow to elbow with people and there are hundreds of people there. What’s the worst he could do? I did as he asked and when I opened my eyes I saw a big bag of white powder in my palm. I gasped and clenched my fist, shoving the bag back in his hand. “What?”, he said, “Do a couple bumps in the bathroom.” Then he winked. Barf. It is 12:30pm on a Sunday, sir! And we are dining at a fine, family restaurant, where my friend is the manager! What’s wrong with you?

We leave and, unfortunately, have to walk the same direction to get to our destinations. While we walk, he repeatedly pulls this bag out to do bumps off of his key. Once he did it in front of a church. Once he did it in front of a playground, as a mother pushing a double-wide stroller walked by. We’re a block away from his job when he ducks into an alley and asks me to wait a minute. I glance over after a few seconds to catch him pissing behind a dumpster, cocaine in-hand. He zips up and we continue this romantic stroll to his job, where he leans toward me, open-mouthed, tongue-first. I put both arms between us, on his chest and push away. “K, this was fun! Talk to you later!”, I blurted out. I’m a fucking liar. Once again he tells me, “I’ll Venmo you!” and I briskly walked on. No look of longing as I left. No eye contact at all actually. I stared at the ground and moved my legs as fast as a girl can in wedge sandals. I’ll never forget you, Venmo guy.

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When grown men lose their shit

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I recently went on a swiping spree, as one does when she is bored on a Wednesday night. I had about 20 conversations going with different guys, which most of us know, usually go absolutely nowhere and you never meet because they all seem boring as hell. One guy took it to the next level. He asked me to meet and get drinks! I love drinks. I live for drinks. Plus, this guy had some hot abs in a couple of his profile pics. I was in.

Admittedly, I am only chatting or meeting any of these guys when the guy I actually like a lot isn’t giving me attention or making plans to see me. We aren’t exclusive…I don’t think? Who fucking knows anything these days. These other boys are just keeping me busy so I don’t psycho text my main guy. Also, I’m not putting all my eggs in one basket. Gotta keep my options open, just in case!

We plan to meet at a place between his place and mine at 7 on Saturday. Cool. Until…the guy I’m enamored with says he will meet me. All bets are off, Ab Guy! My boyfriend’s back! He texts me to confirm our plans and I tell him I had to stay late at work and I also forgot I promised my friend I’d attend his drag show. Yes, I lied! Yes, I’m an asshole! No, this was not the first time and I’m betting it won’t be the last! I asked if we could reschedule. Here was his response:

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Boy, bye!

Should I have kept the date? Yeah, probably. It’s rude to cancel last minute, I know, but shit comes up! In this dating land, you have to be flexible right? I’ve had guys reschedule dates with me and I just go with it! I don’t expect that their life is revolving around me – YET! I think I dodged a bullet with ol’ Tom here.

My First Bumble Nightmare

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Immediately after leaving my husband I started swiping. I could not WAIT to get Tinder! I wanted it my whole life! The night I moved out I sat, surrounded by my suitcases in my best friend’s condo and she and I swiped and giggled while drinking wine until the wee hours of the morn’. ( Well, until maybe 11 pm. She has an infant so bedtime is early for parents apparently.)

That night I felt free. Granted, I was homeless and without my dogs but free nonetheless! I matched with a guy who was the opposite of my type – computer engineer by day and actor by night, short guy with long, wild hair. We messaged back and forth until messaging turned to texting and that turned into late night phone calls. We finally decided to meet. He wanted to take me to a “fancy” restaurant which was his favorite place in the city. I was pumped! My first date!

That Sunday while shopping with my friend, he texted and asked if I wanted to meet at Dave and Buster’s. Dave and mother fucking Buster’s?! Not the fancy place I was expecting but I was going with it. My friend immediately insisted I abort this mission because the loser vibes instantly hit her. She’s far more perceptive than I am.

I got dressed but not overdressed and ventured to our meeting point, as awful as it seemed. The floor was sticky, children were running amuck and I felt like Zsa Zsa Gabor if she were to walk into an unkempt barn surrounded by wild chickens and pigs, flinging horse shit onto her Dior gown. I was in actual hell. “Fuck it,” I thought, “man up and do the damn thing.” So I did. I ordered a beer from the sweatiest human being I’ve ever laid eyes on. I sat and nursed that beer for 45 full fucking minutes waiting on this asshole. Just as I was leaving, I was hugged by a smelly imp. He looked like a warped version of his pictures. He looked like my Mr. Potato Head after my younger siblings rearranged the eyes, nose and mouth to piss me off. My excitement for my first date waned substantially after the whole Dave and Buster’s thing but now it was drained entirely. Gone. It would never return and my head was spinning, trying to think of ways to get out of this ghastly situation. This was my first date though and I had ZERO plan here and no idea what to do.

He ordered a Sprite which was delivered to him in a bucket-sized plastic cup. He slurped it down and we made small talk. He kept smiling and touching my knee and I stared at him in horror and repeatedly moved his hand to his own knee. “Let’s get out of here and get dinner” he said. Fuck yes. The sooner we do that, the sooner I get out of here. He doesn’t have Lyft or Uber on his phone yet, he explained to me, because he just moved to the city from the suburbs six months ago. WHAT!? I didn’t even want to ask and hear an explanation of why he hasn’t taken 10 seconds to download a stupid app so I just got in the cab with him and prayed to dogs that this would all be over soon.

We arrived at our destination. Our fancy restaurant. The BEST in the city. The Cheesecake Factory.