The Countdown is On!


That’s the question, Time Magazine¬†has posed to millions (perhaps even billions…) and you know what the answer [for me] was…



According to this handy little app, which ropes in data from Facebook, I’ve got a whole 2 years 10 months and 8 days to get hitched before I become one of those Late in Life Brides. That puts my wedding date at December 19, 2016. So the countdown is on!! This is how I intend to start all conversation with prospective dates going forward: “Hello, yes, pleasure to meet you. I have approximately 2 years, 10 months and 8 days to make it down the isle. Does that fit in your time frame? Yes? Great! No? Oh, well then I must dash! Time’s atickin’ as they say!

I hear wedding bells in my future! They’re just very faint…

In case you’d like to know exactly how much time you have before reaching spinster status, visit¬†


Oh, and happy Valentine’s Day, friends!


Advice(Maybe), Events, First Dates, Online Dating

Updates from My Sickbed

That headline, it’s mostly a joke. I’m not terribly ill. Just a little on the less than healthy side, it seems. None the less, I’m well overdue for a post and I’ve got plenty of little anecdotes to throw around from the last few weeks. We’ll start with the most recent:

1. In my fatigued state yesterday, I typed out my phone number to a nice young gent on Tinder with whom I had been chatting. After no text for a couple of hours, I figured he had blown me off. And then…. I got a text… from my dad:

Chi Serial Dater  ChiSerialDater  on Twitter

My father and I both got cell phones at the same time, on the same plan. Our phone numbers? identical, except for the last digit. I was very fortunate that my father, a notorious prankster, didn’t send this kid on some wild goose chase. In fact, my father didn’t even respond (so say my mother). And I quickly redirected the charming young man to the correct phone number, double checking each of the ten digits carefully before I hit send. We’ve been chatting. Things look promising. I smell a date in my future!

2. Saturday night I had a second round of drinks with an awkwardly adorable lawyer-type fellow. We met at a bar I had never been to and picked questionable songs from the jukebox (cute, right?) Then we headed out, grabbed a bite to eat, and he suggested we follow it up with one more drink. We shuffled our way through the frozen tundra that is “chiberia” (as they call it), and found ourself in one dive bar after another. We wound up in one of my favorite local spots where he sipped on whiskey and I savored a pinot noir. We chatted about all sorts of things and bickered about the merits of professional basketball players (my official position: those guys are hacks!) We closed the place down and shared a cab (no worries, mom. We made two stops. He dropped me off at my place, safe and sound.) This was our second 5+ hour-long date in 3 days (the previous, on Thursday night) and things were looking pretty promising. But then… eh, nothing. I’ve received a total of four texts from the kid over the last week, all in response to questions asked by me. He mentioned he “hated texting” but, I mean, commmmmeeeee onnnn. Nobody hates texting. Whatever. The kid’s got my number. If he feels like texting me ever, well, we’ll wait and see.

oh well

3. This guy with really, really good intentions cooked dinner for me. He made cabbage and spicy sausage…


So that was a thing.

4. HowAboutWe baited me with half off the membership fee and I bit. So far, only nibbles from single men out there. The format: you write a status “How about we….[insert cute/charming/witty date idea here]”. Status goes out into the HowAboutWe community, where interested parties can click the “I’m intrigued” button. Which is all good and dandy but, as far as I can tell, nobody ever gets beyond the intrigue. No dates coming my way from HowAboutWe any time soon. On the upside, if not a single man gets his act together enough to be more than intrigued by the time my 6-month membership is up, I get my $30 back. Yippee…


5. Meanwhile, during my zombie-like sick state, when I’m not busy coughing or sleeping, I’ve been prowling the internet, finding the finest, most eligible bachelors Chicago has to offer. Here are my findings:

UntitledA nice little selection, representing the great options available on two different platforms (OkCupid, HowAboutWe, hyperlinked, just in case you want to seek any of these guys out – they’re all single! And looking to mingle!)

That’s all to report at the moment. Once I stop with this disgusting cough, perhaps I’ll land a few more dates. In the meanwhile, my plans for getting healthier look something like this:


Have a good weekend, y’all and have a drink for sick ol’ me on this snowy Saturday night!


“Spontaneity is fun” said the man I met on Tinder. And you know what I thought? “But I had plans to paint my nails and eat green beans.”


This isn’t a real post, I was just trying to be spontaneous.
Time for green beans.



Earlier in the fall I met this incredible woman who showed me that my hair really looks better in a refined, structured lil’ cut rather than long and, as one ex once put it, scraggly locks. But how great she makes my hair look is neither here nor there in this post. On the other hand, how great she is as a person, is the basis of this post! It turns out she’s diving back into the Chicago dating scene (competition is on, girl! Dukes up!) after her last person-of-interest “fell off the planet” (I think that’s how she put it). As we chatted about it over Facebook, we both lamented at how those men who go AWOL are THE ABSOLUTE WORST. But then…. I realized something…

So here’s some background: As per usual, I’ve spent the last few months going on dates. One particular gent snagged my attention more than others and his kindness and generosity kind of sucked me in a little bit. All in all, over the course of about two months (including the holiday season) we met up about half a dozen times. He was super sweet, cooked me dinner (twice!) and I was really comfortable around him. So I figured I’d wait it out and see if a spark came around. When it didn’t, well, you know, my schedule started to look busier and, uh, I started forgetting to text him back (honestly unintentionally! I swear! you know how it goes, right? When you’re excited about someone you text them back IMMEDIATELY. When you’re not, you see the text but decide to finish whatever project you were occupied with and before you know it, it’s 24 hours later and you haven’t responded…) And all of a sudden I’m that awful AWOL person! Crap, right?

And thus, here’s my question – I’ve been dumped by a handful of methods. Once, in high school, I was dumped via Facebook (to be fair, I stopped answering his calls…) And it seems the general consensus is that some methods are abhorrent while others more acceptable. Breaking it off by email? Hell no. But calling me up and showing up at my apartment to have “a talk” about how we probably shouldn’t see each other any more after casually dating for a month and a half? Well, that was a bit excessive too. And certainly far far far too awkward. So Question 1: When is it actually a Break Up with a capital B that requires formality and anxiety and possibly tears, and Question 2: how does one really gracefully bow out of something casual that isn’t progressing as hoped?


100% certain


Now, to be fair, I’m not sure the exact depth or breadth of my friend’s relationship situation so I’m not putting myself on the exact same playing field as this guy. But, I’m genuinely curious. What’s the best way to get out of something casual, with someone who is genuinely super nice, just not, you know, The One?

Colin firth

First Dates, Online Dating

“Back” in the Swing of Things

After two weeks home in Michigan and practically a third week off from work, I have successfully:

1. Gained a million-and-one pounds (primarily in wine and Christmas cookies);

2. Painted my bathroom a godawful shade of blue;

3. Cleaned my whole apartment;

4. Watched three seasons of SVU;

5. Failed to go on any dates and therefore failed to maintain my blog. Whoops.

Good news, my friends! While I may not be back into the professional swing of things quite yet (give me a few days…), I’ve strapped two dates under my belt in the last three days. Back in the saddle! Because, well…

tswiftMe too, T-Swift, me too.

In other news, I had a date at Glenn’s Diner the other night and it was INCREDIBLE. Their awning says “Best Food in the World” and while I don’t know how accurate that is, I do know that they had a CEREAL WALL that was stocked with every childhood cereal you’ve ever dreamed of. While I enjoyed a delectable Lake Superior White Fish, I had my eye on that box of Count Chocula alllllll night. Damn. Read more about it: here

Online Dating

Lords a Leaping (i.e. Men for Christmas)

Picture1When asked what I wanted for Christmas, a new man and a new car were essentially the top two things on my list. Granted, my dad would do a stellar job at picking out an affordable, reliable vehicle to truck me around the city, but I started to get curious about what kind of suitor my family members would wrap up and put under the tree if given the chance.

Probably, my mother would snag me a dapper (and tall) Canadian gent. Liberal thinking, who likes to wear buffalo plaid, and knows how to sail a laser. He’d have to be able to play card games without getting too rowdy, enjoy washing the dishes after dinner, and, of course, would be able to craft a stellar G&T. A rugged yet refined, educated lumberjack with a 9 to 5 and high IQ.


My mom and I have pretty similar taste.

My dad on the other hand, I can only begin to imagine. He’d probably find some goofy hooligan who he could count on to be up for picking the most ridiculous paper to wrap my guy in (something with a repeating pattern of J.Biebs or OneD) before leaving him under the tree for days/weeks so as to deter my suspicions (secretly feeding him only at night once I’ve gone to bed and never ever sneezing.) Mandatory skills include golf, yoga and a propensity for bad puns. A laid back attitude paired with a well rounded mental database of all things science-related, ranging from bird and plant identification skills to conversational knowledge of lipid mediators and Citrullination. Whatever those are.


I think I may have actually gone out with this guy on Tuesday (minus the golf/yoga bit, plus a bit of knowledge about fermentation as it pertains to brewskies.) Second date on the books for Monday

I think… that my brother… would, hmmm, uh, maybe, Send me one of his MBA buddies? Or pull some wine & cheese loving, foodie, [successful] vineyard owning hipster. Or a tech/finance nerd. An engineer? Interest in travel would be appreciated, I’m sure. The seal of approval would come once he knew what kind of books the guy kept (and once he knew his income.)


Fun fact: Ashton Kutcher studied engineering before he realized how attractive he was. Fun fact: Steve Jobs was a brilliant wackadoo

Update: upon reading this post, my brother told me I was way off base but also refused to correct me. He also told me to stop writing about him on my blog. Like that’s going to happen!

Obviously, Jake the Cat just wants me to stay single.


That said, we’ve got some irons in the fire despite the hectic holiday season. Holiday dating is a trick (can I get an Amen?). How the heck am I supposed to make time for cocktails when all I can think about is sugar plumps and twinkle lights?? And it’s no fun to do the romantic holiday dates with someone you’ve just met (although a Zoo Lights date is in the works!) Plus, my Tinder activity has severely dropped off since discovering QuizUp. I guess I like being smarter than people more than I like being judgmental (ha)

So blogosphere, got any tips for holiday-style dating? And more importantly, what are you asking for this holiday season?