Tag Archives: bad online dates

Bullet Point Tuesday: Weekend Update

I love when people try to talk to you about dating and throw all sorts of cliche phrases at you, in hopes that suddenly you’ll either be enlightened or more hopeful or less likely to polish off the almost full gallon of Eddy’s that promises to make you feel better than any boyfriend ever could.*

Some of my fave mantras that get thrown a single’s gals way are: “It’ll just happen when you least expect it.” Well what the hell, if we’re really honest here, we’re kinda always expecting it (preferably in a JLo/McConaughy way), so according to your theory, it’s never going to happen. OR: “You just can’t try. Let it happen.” Yes. Because that’s what online dating is about. Letting shit happen naturally. OR: “It’ll just start all of a sudden. You know, when it rains, it pours.”

Pours what, though, no one really specifies that part of the prophecy. Because there was some pourage this past weekend, but I don’t think it was in the way the hopeless ro’s anticipated.

  • Friday: Date #1, 5:30-7:30, Happy Hour Drinks and Appetizer

I should start recording the crestfallen looks on guys’ faces when, at the end of the date, we both stand up together for the first time and he’s looking up at me. Can you imagine the You Tube video montage that would make? Just a bunch of these. Not that I don’t empathize with these guys. I imagine it’d be to similar to standing up and realizing that, even in flats, you’re still taller than your date.

  • Saturday: Bar scene, where every couple dreams to start their love story 

I hadn’t openly hit on a guy in a long time, but last Saturday I had just enough of Lottie’s champagne** to muster up some courage to ask this homeboy to follow us to our next destination, Cortland’s Garage. He must’ve been drinking the same champagne because he mustered enough courage to come…and then talk to two hot blondes the entire time, while I chatted up his friend. So I played wingman for myself. Just one of those times I wish I wasn’t so damn good at it.

  • Sunday: Date #2, 12:00-2:00, Brunch (yes, rolling out of bed and putting on makeup before 2:00 was rough)

Dude was so sweet. So sweet. But, honey, at 34, why do you live with 5 other people you met on Craigslist? I dunno. I get that not everyone is as comfortable becoming besties with credit card debt as I am, but some for things I just encourage the splurge. Like an apartment that’s not reminiscent of the Duggars‘ household. Or Single White Female.

Some people would look at this past weekend as a failure in the Game of Love. But those are probably the people who think this is cute and do not like this. Plus, things are already looking up. Yesterday a 58-year-old suburbanite messaged me with “LOTS” of interest. I mean, when a Baby Boomer puts something in CAPS, how can a girl not be flattered?

*If my Lipsticks are reading this, I’m totally kidding. There is definitely not chocolate chunk cookie dough ice cream in my fridge. 

**What can I say? I’m classy like that.


Lies That Online Dating Told Me

If you’ve ever seen any commercials for online dating, then you’re familiar with the handsome, well-dressed, young professional make the claim that he wants to try it because he’s “really busy” and “just doesn’t have time” for dating. And Match or Farmers Only* just makes it so much easier to fit dating in a super busy/handsome/well dressed schedule.

And if you’ve ever tried online dating, you know that this is one, fat, effing lie.

Online dating is like a part-time job. A part-time job that pays largely in disappointing dates. (“At least you get free drinks!” non-single friends will say. I just pat them on the hand. How cute.)

While I used to be embarrassed about the stigma of online dating, I’ve completely embraced it as an acceptable way to meet someone. Or to at least have the best story at the next cocktail party. Not to mention, it totally takes the pressure off putting on make up before I go to the grocery store because I just might bump into a cute guy who not only shares my love for baby spinach, but wants to take me out to dinner to discuss it.

In fact, I’ve become so accustomed to online dating, that when a guy does approach at a bar, I’m completely thrown off. For example, the other night the fabulous CBN ladies and I enjoyed the now infamous Movie Monday at ROOF on the Wit. (Btw: While there is a movie, it’s totally up to you if you want to watch it. Good luck trying to get me to pay attention to 21 Jump Street while there’s endless liquor and conversation about grilled cheese with food bloggers.) And as we were chatting, a guy approached our table and began conversation, seemingly because he knew someone. When I inquired about the connection, they looked at me blankly. Oh. He was hitting on her. How retro.

While online dating is time consuming, I’ve found that the bar pick up scene is starting to dwindle. Or maybe I’m just wearing heels more frequently. (Why are men intimidated by tall women? It just shows we have confidence. And could kick your ass. In heels.)

After my last date (re: My Date With a Hipster), I’ve decided to just start eliminating assholes from the get-go. Which, I now realize, has turned me into one myself….ok, right, so not much has changed. Please see following Tinder conversations for proof:**

Exhibit A
  • Tinder Guy #892: Yo! East Bank Club party was fun. Cougs were out in packs hunting. Stopped by the mid and called it a night. Last night was Boundry Lumen then the Mid. In the burbs now. What did you do. 
  • Me: I need a translator for half of that shit. Mid what? Way? Like the airport?
  • Tind #892: It’s some stupid night club on Halstead and Lake. Cougars are single older ladies that go after younger men. 

A. If you live in Chicago, you know what the East Bank Club is. I can only assume that the name dropping of those other places indicates that they are on the same level of dbag and washed up Abercrombie models as EBC. I was just too lazy to Google the Mid, Boundry or Lumen. (Still not sure if Boundry Lumen is one place or if Boundry is incorrectly spelled, like Halstead.)
B. Thanks for the heads up on the cougs definition. I suppose adding the “ar” would’ve been too taxing.
C. No, I will not go out with you.

Exhibit B
  • Tinder Guy #923: What’s the weirdest question you been asked on here?
  • Me: Um, that one.
  • Tind #923: Hahaha. [I wasn’t kidding.] Do you live in the burbs or city?
  • Me: Does anything about me suggest suburbs, 923?
  • Tind #923: No, but you never know….I live in the burbs. 
  • Me: Uh oh. 
  • #923: Uh oh? [Great. Not only does he live in the suburbs, but he also doesn’t see the problem with it.] Yeah, I’m out in [name of suburb]. I work for [name of university].
  • Me: Oh nice. [hoping I’d just landed a professor] I’m out that way from time to time. What department?
  • #923: Residential Living. We should grab a drink when you’re out here.
  • Me: [silence. forever.]

A. Nope, don’t think I’m going to hit up the dorms in the suburbs and crack a Natty Light with you. Even if I’ve hit rock bottom. Even if I’ve hit a Bynes/Bieber/Lohan rock bottom rolled into one messy burrito. Because then I’ll just seek my burrito treatment in seclusion like a respectable person. And then blog about it.
B. How did a suburbs guy weasel his way into my Tinder feed when it’s set at a 4-mile maximum radius? I feel catfished. (That hyperlink was for the Baby Boomers who read my blog. You’re welcome, Dad.)

This is the problem with even simple online dating, like Tinder, which doesn’t even require reading. Just classic, shallow, snap judgement, but even that becomes time consuming because I find myself in mind numbing conversations about the suburbs or fishing. (Maybe the fishing guy got lost and thought he was on Farmers Only.)

But, like the dedicated researcher I am, I’m going to continue in my quest for the perfect online dating system. One, preferably, that finds me that 6’6″, Australian-born, sarcastic and soulful man that I know is out there. Just waiting. Behind his computer.

Yeah, nevermind. He sounds like a creep.

*Does anyone else want to try this out of sheer curiosity? Their slogan is “City folks just don’t get it!” I’m dying to know what I don’t get. Aside from milking cows and anything that involves getting up before 8 a.m.

**Upon going to my phone to pull up said conversations, I got distracted and Tindered for a good 12 minutes. Or 32. This thing is like online dating crack.


My Date With a Hipster

I try not to stereotype, but this summer my experiences with hipsters have not done much to progress a positive image in my mind. First there was Pitchfork. Listen, I’m the last person that wants to interrupt a solid discussion about thrift store midriffs, but can someone just answer if they’re waiting in line for the Porta Potty? Also, when you bump into someone and spill their beer all over them, you apologize. You don’t laugh in their face. This isn’t New York. Hipsters: We expect more from you. Or I did anyway. And then I went on a date with one.

In efforts to expand my Tinder endeavors (no, I will not concede on my maximum 4 mile radius; there is nothing more annoying than a guy who is geographically undesirable), I decided to go out with a guy whose pics normally wouldn’t get the right swipe, but they were definitely funny. In one picture, he’s cradling some large, fuzzy object with a look of terror. I dunno. I’m a sucker for irony.

It’s not that I have some super high standard for attractiveness when it comes to guys. In fact, I find the gelled up arrogance of Abercrombie replicas quite the turn off. Which is why I immediately “X” any guy on Tinder who’s posted a selfie or pic with no shirt.

But because my friends have hinted that maybe I pigeonhole my dating life a bit in search for of a rough around the edges, yet still soft-souled, 6’6″, sarcastic and creative type (he’s out there!), I decided to expand my Tindering acceptance level. And that’s how I found myself on a date last week with Hipster.

Our texts back and forth leading up to our date were in line with his photos–hysterical. And even though he didn’t look the role of my walking oxymoron perfect match, I was looking forward to our date because of the witty banter we’d exchanged, which was primarily about cheep beers and avoiding bars with dbags.

It’s been years of this dating game, and I can’t decide if my expectations are too high, too low, or irrelevant when it comes to dates. But is it so much to ask that on a first date the guy shows up on time, pays, and isn’t high? Because Hipster didn’t meet any of these requirements.

After I waited ten minutes at the bar by myself, Hipster showed up. I didn’t see him walk in, but just heard someone behind me give a gruff, “Hey.” I turned around to see a bearded man holding a mini cup of soup. “Want some soup?” he asked. I stuttered some form of no. He shrugged and began picking pieces of corn and beans from the plastic cup.

I needed a drink. Immediately. Flagging down the bartender with childlike desperation, I then turned to ask what he wanted and subsequently made eye contact with him. Staring back at me was a set of wild eyes. Awesome, Chloe, you finally landed a crazy one. Wait, why are his pupils so small?…I watched as his soup fingers continue to pick out small morsels of various vegetables. Oh God. He’s high.

Though I had a contingency plan in place, I was debating if I should just bail immediately. Hesitation got the best of me, and we got our drinks. A Stella for me and Negroni for him, because apparently his high wouldn’t be complete without 3 different kinds of alcohol. We grabbed seats outside, and his pupils remained the same pinpoint size, continuing to give his eyes this crazed look. I felt just as comfortable as a Kardashian in an Aldi store.

And the date commenced. If you could call it that. I mean, we did cover topics like work, family, and hobbies. At one point he asked if we could go visit my brother. Like right then. Just hop in his car, drive to the suburbs, and hang out with him.

Being a hipster, he of course knew all the latest, amazing, underground restaurants in the city. It’s not that I don’t appreciate these places; I just don’t keep up with them. Which gave Hipster smug satisfaction to say, “Really?! You don’t know about Such-And-Such-Place?!” No. Clearly I’m not cool enough because I don’t do heavy drugs, follow the hottest chefs, and smoke from an ecigarette (“to be polite”).

I did recognize Parsons Chicken N’ Fish–only because Tinder took me on a date there last week–and when I raved about it, Hipster asked if I wanted to go. Right then. Just hop in his car and go. Whatever this guy was on really made him want to do things immediately. At least he doesn’t procrastinate.

It shouldn’t have been a surprise that we both finished our first round in an aggressive fashion. Hipster made slurping noises with the last of his Negroni. And I waited. We were clearly playing chicken about buying our next drinks. My desperation to get another beer and get a breather from him got the best of me, and I offered to pick it up. The damn Negroni was $7. Effing hipsters.

Towards the end of the conversation, Hipster apparently thought the date was going so well that he decided to let me know he’s Jewish. And he hopes “that’s ok.” I wanted to tell him that was about the only think “ok” about him.

Finally my deadline approached with my fictional plans to meet my friends’ kickball team for their end-of-the-season party (what???). I pulled a double dodge move to his attempt at a kiss and offer to drive me to my next destination. I of course immediately went to Daisy and Lexi’s to debrief. And to Google what drug makes your eyes do that.

Naturally, I’ve relayed this story to several friends, and the initial response is surprise that I hung around for so long (1 hour). Do we need to start having contingency plans for contingency plans? Is it acceptable, when my date shows up with soupy hands and opiate eyes, for me to simply just walk out?

I’m not sure, but I am sure of my new Tinder tagline: Non-compatible with hipsters.


Why Dating Should Be Taught Instead of Drivers Ed


I must’ve been Amanda Bynes in another life. It’s the only explanation for my dating life.

Last week I went on a date from the same online dating site I’ve been using. I gauged that the guy was rather corny, as his emails consisted of questions like, “What superhuman power would you have?” or “If you could be a utensil, what would it be?” He said he’d be a spoon because “spooning is fun.” I told him I’d be a cheese grater. He did not understand that I was metaphorically ripping him to shreds. 

Against my better judgement, and in efforts to “get out there,” I decided to meet up with Spoon. The day before he asked me if he’d get extra credit points for picking a creative date idea. I told him I don’t grade in the summer, but sure. 
His first “creative date” idea was to go to a bar in Wrigleyville. Where he also bartends. I told him that unless he was an 18-year-old frat boy, there was certainly nothing creative about that. 
The second idea was to go to a trivia night in Wrigleyville. Apparently something about sticky bar floors and wasted underage drinkers really makes this guy feel romantic. Or perhaps even like spooning. 
I agreed, as long as he understood that I am horrible at trivia and not competitive. So if we could lose without him yelling at me, then fine. 
I ran into a bit of trouble trying to find him in the bar because there was only one guy sitting alone, and he didn’t look anything like Spoon from his online profile. I knew he was already there because when I told him I was running 15 minutes late (typical), he said he found a spot.
Awkwardly, I looked around the bar as waitresses smiled kindly at me. My face grew hot, and I kept staring at my phone for a miracle. Fuck, I’ll just call him. He answered. I looked over to where a guy was waving. He was sitting with two friends. 
You’ve got to be kidding me. 
Thus began the night I went on a date with three dudes at once. We made our own trivia team, and I decided to pretend like it was my own mini-Bachelorette series. I mean, it was pretty much the same situation: alcohol, dbags, and vying for attention. 
However, all three were eliminated rather quickly when it came time to select a team name. They couldn’t be more enthusiastic about calling us My-Mom-Doesn’t-Wrestle-But-You-Should-See-Her-Box.
I can’t make this shit up. 
As any lady would do, I chose to house some beers at this point. The only answer I knew all night was about Sex and the City. Two and half hours. And all I had to offer was Elizabeth Taylor. (Trivia Question: Who was the Lifetime show about that Charlotte was watching after her miscarriage? C’mon, give me a challenge.)
Spoon caught onto the fact I wasn’t having a stellar time, so he made intermittent conversation and, after a bit of prying on my part, revealed that he lives with his parents. At 32.
And, of course, we had to go to one more bar, and of course, it was the bar in which Spoon works. The night ended with a one-armed hug and me hustling into a cab. 
Who is not teaching these guys the rules of dating? Why do they think it’s acceptable to bring friends, go to the bar they work, skip the Bears game, make fun of poor people, sniff wine, or wear those awful soccer sandals on a first date?? I vote to replace Drivers Ed with a course in Dating. But the Drivers Ed teacher is not allowed to instruct it. I have a feeling we’d be no better off. Sorry, Mr. C.

So I just joined Tinder (judge away), and within a day I already have a date set up. I guess that’s what happens when a dating site is shallowly created solely on looks and geographical location. People will go out with anyone. But we all know I’ve been doing that anyway, so don’t worry, expectations are still bottom-level low. 


My Date With Daniel Tosh: Minus the Funny

This past Friday was my first online date in four years. Because I’m slightly paranoid, online dating makes me pretty apprehensive. I’ll lie about my last name, actual location of my apartment, and job until I’m sure this dude isn’t going to go all Mark Wahlberg in Fear on me. Which I imagine would take a good 3-4 months.

So I had every contingency plan in place: meeting in a public space; friends knew when and where; dinner plans with Brooke at 8 for an exit strategy; my outlook was optimistic but not overly hopeful; Mace was packed in my purse.

The plan I forgot: what do when your date is extremely offensive.

As my students and exes can attest to, one of my biggest flaws is giving a person a second, third, or 18th chance long after experience should have taught me not to. It’s why I’ll go out on one…or four too many dates with a guy.  It’s also why my students just laugh when I give them a “final” warning.

So if I say that within the first three minutes of sitting down with this dude that I could tell there would be no second date because he was a horrible human being, that means that he and Kim Jong-un would probably get along swimmingly.

Throughout the course of our hour and half date (aka the longest two beers of my life), he proceeded to rip on the waitress at the neighboring patio, the couple at the table over, and hipsters walking by. The latter was especially ironic given his skinny jeans and black hoodie.

Now this may come as a surprise, but I don’t enjoy making fun of strangers. However, once someone opens their mouth, then anything is fair game. Then we’re not strangers anymore.* I think that’s fair. Equal opportunity ridicule.

Which is why it took all my energy not to start laughing when homeboy told me he quit his first job out of law school because the firm was “too greedy.” Apparently his fresh legal skills are so paramount, they’re worth going back to live with your parents. 
Likewise, when he bragged about punching a freshman track member his junior year of high school, I restrained myself from asking if he had a commemorative plaque for the event. In his room…in his parents’ house.

But it was when he began to throw around complaints about “low-income” and “poor” people, that I found myself in a precarious moral dilemma.

As he droned on with his offensive comments, I seriously weighed my options. I could:

  1. throw my beer in his face 
  2. leave 
  3. have another beer and hope time moves faster

It was quite the inner conflict. I’ve always wanted to try #1, and I’m broke enough to justify #2. But I ended up with the last option. And here’s why:  During homeboy’s incessant ranting, which also included a slew of daddy issues, his insecurities were as transparent as when I wear make up to the gym. And by acting mean in return, I wouldn’t be changing him or his ignorance. In his mind, I’d only being justifying it.

So at 7:36, thankful for my exit strategy, I told him I had to get going to make my 8:00 reservations. Which were a block away. At Brooke’s apartment.

As we walked away from the bar, he said he had some Groupons that were about to expire and asked if I wanted to use them with him in the next few days. For a guy that makes fun of poor people, he really knows how to wine and dine a girl.

I got a text from him on Sunday asking if I wanted to cash in on those Groupons. I told him that I just didn’t see us connecting on a romantic level. I had a few cocktails in me at this point, which I think is why I was overly PC. He wrote back a snide response, which included throwing in that I’m too tall anyway.

I should’ve thrown the beer.

*This excludes celebrities, who are, of course, fair game. 

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