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  • Writer's pictureCarey Tedesco

The Adventures of Online Dating and How I Have Zero Game

After being separated for a little over a year and currently going through a legal separation, I decided to dip my toe in the online dating pool. I’m not really ready for a relationship or to even actually date yet, but out of curiosity I found myself wondering what I might expect when I am.

I started by taking a decent headshot of myself that I needed to do regardless for my LinkedIn profile and my website. I found a few relatively recent photos and wrote up my bio. Depending on the website, my bio ranges from a quick description of “Art Lover. Blonde Shorty. Starbucks Addict. Comedy junkie. Indie music lover. I appreciate people who are introspective, self-assured, and have an acerbic sense of humor. Must love dogs.” to “I’m a graphic designer, mom and… boring AF.”

I went through the motions of agonizing over how to describe myself with the “fun” Q & A questions. Like “The world would be a better place with more…” I put “tacos”. What I really wanted to say was that I have absolutely no idea what to say. Love and kindness just seemed so cliché and I am anything but a walking cliché (or so I thought). I then typed in all my preferences for what I was seeking. You know…

A tall, handsome man between 45-55 years of age, lives within 45 miles of me, loves dogs, interested in art and music, and not a stalker or a creep. (That last one is an option I think they should add.)

First off, you have to know that I have no game. No game face. No sexy selfie photos. In almost all of the good pictures I could find of myself there is either my ex-spouse of 20 years, one of my kids, or one where you can visibly see my wedding ring. But I kept digging and settled on five pictures: one serious photo (my work photo), one fun (I’m kissing a Prince Eric cup because he’s so dreamy), one of me relaxed on a trip to Boston with my family, my dog in the tree farm behind our house, and a Buddhist saying. I sat back to find myself petrified of how I’m going to appear. Will I look too old, too short, too curvy, too serious? Do my eyes look weird? What do the other women look like? Then I’m thinking about how I will sound. Will I sound boring, too needy, trying too hard?

The Reality: Probably. Then I said fuck it and threw myself out there.

Guys. I have no idea what’s happening on the other side in this online dating world. No clue as to what my fellow ladies are sharing. (Though recently one of my divorced dad friends showed me there are some serious skanks out there asking for dick pics and airing out their goodie bags like sex workers…) Okay, so, but HOLY HELL ON A HOT DAY! Apparently half of the men my age are into extreme sports and want a lady to run a triathlon with them. I was visually invited to many male gun shows (“Sun’s out, guns out, babe.”) The other half of the men looked like they were 70. I had to go back and check three times to make sure I put the correct age in my preferences. Yep. Same age range. 45-55. And no matter what site you’re on, they always go higher for you. Never lower, which I found really interesting. So, they figure all of us ladies are not interested in younger men I guess. I mean, of course we want WAY older guys because they want younger right? Ugh and ugh. I’m not going to go there.

So, the best were the profiles that I now collect with screen captures and have saved in a folder on my phone titled “HOT GUYS”. I recently showed them to two of my best friends who are a married couple. I burst out laughing when I saw the husband’s eyes widen. They couldn’t believe what they were seeing and asked if these were real people. Another one of my good friends said he needed to sanitize his phone… or burn it maybe… then pour gas in his eyes. I’m pretty sure I will get sued if I shared my collection of HOT GUYS so you will have to envision what’s out there by reading through my experience.

For those not in on the online dating scene, and in the know about swiping: it’s left for No, right for Yes. I pushed my inhibitions aside and started swiping. Here is what my internal monologue sounded like:







Serial Killer.


Put your shirt on.

OMG. Please put your shirt on!

Is that a walrus?

Is that a drag queen?

Drug dealer.

Drug addict.



I’m going to die alone.

Then it happened! I found one! A good looking guy with a fantastic profile. He was honest, funny, sarcastic, and even loved dogs. Apologizing for not having bathroom selfies and making fun of himself for being incredibly tall. I swiped right and sent a text. I was so excited to see someone who I could see myself with. He met my criteria: self-deprecating sense of humor (check), sarcastic (check), tall (check), and loved dogs. (check!) I sent back an equally sarcastic and silly text introducing myself. (Remember, zero game girl here.) I thought I would be witty and write a response matching his profile. It wasn’t short, but I didn’t think it was too long either. I hit send and waited totally oblivious to how this whole online dating scene worked. I thought, he’s got to respond. I’m his equal! Yea, I’m like a foot shorter than him, but what I lack in height I have in personality, right? Right?!

Nope. When I looked over what I wrote I realized that I had no game. I was too wordy, not flirty, too honest, too vulnerable. Yeah, I know, yuck. I even sent a follow up text apologizing for being a dork. (I can feel your facepalm, because it’s what I’m doing right now.) At the time though, I didn’t really get it. I thought, oh well. I guess he wasn’t into me, so it wasn’t meant to be. I was slightly deflated but decided to give it another go. I went through another swiping round similar to before (adding Scorpion Necklace King guy to my file), I swiped right a few more times. The man that liked me back was cute, had a kind face, and had a very genuine, laid-back profile. He sounded grounded, he was local and had been divorced for 10 years. And guess what?! I blew it. You knew that already though, come on. I blabbed out my life story within the first text exchange. This poor man was like “Wow. That’s probably the most detailed first meet text I have received.” (More facepalms over here. Even now as I’m writing this.) Clearly, I was not ready to date. He was super nice and somehow got over my very informative text. We had a few friendly text exchanges within the next month and became friends on facebook. Thankfully, he hasn’t unfriended me yet and if he does, I seriously wouldn’t blame him. I mean who shares all their shit right out of the gate? Me. That’s who.

And at the same time, clearly I can laugh at myself in all of this. Through pain there is growth. Failure is a part of the road to success. I’m a lady who has learned, and continues to learn a lot from her mistakes — and not just the ones with online dating. A lady who is working on herself to stand tall and remember who she is. That when she is ready, she will brave the world of dating. One “Blonde Shorty” who loves dogs, and is a liberal thinker. And as I have been told recently by a new guy friend very who is also sorting through the mire himself, I am a woman that has an infectious laugh, a big heart, no shortage of candor, and a quick wit. I am treading lightly, focusing on healing myself, and in no rush to date anyone. Truthfully, I think I need to date me for a while.

With some of the knowledge I gained, I figured it might be good provide some tips to help the guys out there who want to meet a nice lady who is looking for a LTR. (Long Term Relationship, keep up) So here we go. The disclaimer is that if you’re just looking to have fun, by all means do the opposite of what I’m saying. (Remember, I have zero game, so this all means nothing.)

Carey’s Do’s and Don’ts for online dating profiles:

Don’t: Post photos of your dog with it’s tongue in your mouth. (Yes, I have really seen this.) No snakes, or reptiles please. It full on creeps us out.

Do: Post photos of you walking or playing with your dog or cat. Hell, even just your dog or cat. It says you like animals and that’s a good thing.

Don’t: Post pictures of yourself when you were younger. It tricks us at first and then we are annoyed and feel duped.

Do: Post photos of how you look now. Be the age you are and be damned proud of it! It shows you have confidence and that you believe age is just a number, because it is.

Don’t: Post bathroom selfies or selfies with your shirt off and the hint of your crotch visible. We can tell you have a nice body just from when you are wearing jeans and a t-shirt. Don’t worry, if we like you we will rip that shirt right off your toned chest.

Do: Take the time to go outside and ask a friend to take some pictures of you while you’re all hanging out. Do a group selfie or just have them pretend to be a photojournalist while you’re in your natural habitat being the kind and cool guy that you are. (No holding babies please. We know that’s all bullshit.)

Don’t: Write a profile that’s a list of what you want like it’s a list of demands. For example, “I want someone who’s a good cook.” (Do I get to clean too?) and “Must be athletic and share my interests”. (Is this guy a drill sergeant?) It’s also just as obvious that you’re trying to be a suck-up when you write that you’re looking for your soulmate, say that you are a great kisser, or that you’re waiting for your queen. FFS.

Do: Take the time to write a sincere bio. Not TMI and just a general idea of who you are and what you like to do. Being silly and sarcastic goes a long way. Keep the focus on you rather than a long list of what you want in a woman or your next relationship. Leave your baggage at the door and proceed. No need to mention that you don’t want drama. It makes you sound like a dick and most of us don’t want drama either which is why we’re on a dating site to begin with.

Don’t: Post selfies from inside your car. You look like you might be cheating on your wife and looking for a hook-up.

Do: Get out of the car and take a selfie of yourself with a scenic background or even just in your backyard. And blow off including the fancy car you drive all together. It’s too flashy and you want us to like you for you, not for your cool car.

Don’t: Post too many pictures of yourself being extreme sports guy. I get it. You’re active. You snowboard, ski, jet ski, waterski, surf, paddle board, windsurf, motocross, BMX, Mountain Bike, bungee jump, and like jumping out of airplanes. You’re a guy and most of you are extreme already. When there’s more than one photo, it makes us feel like we won’t be extreme enough for you. Many of us who are single at this age are moms and just keeping up with the day of raising kids that doesn’t really lend itself to that “extreme sports” lifestyle. I will gladly cheer you on any day, but if all of your photos are "extreme" and the point is to show me you’re youthful, I’m good. (See the part about embracing your age above.) And by all means, if you’re looking for extreme sports girl, keep at it. She’ll pop up eventually and will definitely be your soul mate.

Do: Post some photos of yourself doing your activities. Just know that you standing next to your surfboard is good enough for us. (This is where I encourage the shirtless selfie.)

Don’t: Post pictures of yourself smoking a cigarette, shirtless with a walrus painting behind you, looking like, or actually are a drug dealer, addict, or drag queen.

Do: I even need to explain this?

Don’t: Try to avoid posting pictures of yourself in front of a mirror with your cell phone in it. It has the propensity for us smart girls to think you aren’t putting in the effort or are actually technically challenged which I’m guessing you’re really not. We want you to look savvy and cool like you actually are.

Do: Get a friend, neighbor, stranger, or a family member to take a quick photo of you. If you can figure out how to take a selfie without the phone in it, you have my attention.

Don’t: Post photos of your tattoos. Leave that to when you meet and can tell the story behind them. Otherwise it screams you’re shouting for attention. “Look at me I’m still young because I have tattoos!” Same goes for piercings.

Do: Post tasteful photos where your tattoos might peek out of a sleeve of a shirt. It puts a little mystery in there without being too flashy about it. I know I’m curious.

Don’t: Post photos where you’re sticking out your tongue. Just don’t. You don’t look silly or fun. You look like a douche.

Do: Smile, be yourself and show us your pearly whites. If you want to show us you’re funny, we also dig guys dressed up in stupid Halloween costumes. But it has to be from an actual party. Dressing up on your own without the actual story will be a whole other form of shame glaze you will never recover from. (ps. Ralphie in the bunny costume from ‘A Christmas Story’ can never steer you wrong.)

Do: Take some time to think about what we tend to like about men. Here’s what we like: You being you and often that means you being funny. You don’t need to tell us that you appreciate sarcasm or that you are funny, just write something sarcastic or make fun of yourself in your profile. It’s a sign that you’re intelligent and can laugh at yourself. I swiped right on a guy just because of his answer to one of his profile questions. To “What makes a relationship great?” he answered “Fuck if I know!”

Do: Be yourself and be genuine. Keep the sleeves on your shirts in your photos whenever possible. Try your best to look confident and relaxed. A photo of yourself doesn’t have to be a head-on shot where you have a smile plastered to your face for no apparent reason. (I suck at selfies, so I’m not judging. I do know when a smile is fake though, just like you do.) So, get your friends involved. They will make fun of your big boobs, I mean forehead, or whatever. It will at the very least get you laughing about the awkwardness of online dating and definitely make you laugh at yourself. Getting comfortable with the uncomfortable is what we all have to do when taking this leap forward into the world of dating. It’s a torturous process and as women, we totally get it. And, no. I will never be asking for a dick pic. (facepalm.)


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