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Update: Midwest Man

17 Sep

I’m so behind on posts, I’m just going to plow through them all at once!

And this is a bit of a delicate subject, given that Midwest Man may or may not read this blog. And I know that one of his best friends does (that’s right, C) and will occasionally cut and paste content in an email to him. (Please don’t do that!?)

But for the sake of the leaderboard, I’ve now gone on three dates with him (with a fourth this weekend). He’s GREAT. I’ll write more on these soon…


>Update: Man#1

17 Sep

>So remember Man#1 (let’s call him B), who is a cute hipster but took me to a horrible sushi place for lunch? He texted to ask me out to burgers…that was last weekend and I told him “Sure! I’ll get in touch with you next week!”

But I haven’t.

So can I just ignore him? That’s mean. The alternative is to write and say that I’m not interested, but that’s kind of mean as well. Or I could get burgers with him, but I would rather spend my time with people I really like.


>Date Recap: CFH Man#3, Date#1

17 Sep

>On Monday night, I went on a date with a sweet guy we’ll call Z. Time was running out and my schedule was quite busy, so I penciled him in for a 45-minute drink before dinner with my roommate (which, by the way, I’m going to argue is my (Wo)Man#4).

For whatever reason, it seems like I’m always stuck picking meet-up spots. I guess it’s easy to tell I’m opinionated?

Of course, the cute Japanese sushi/sake place I pick doesn’t have any bar seats. And my back-up bar is also packed. So we end up at a diner nearby, drinking wine (I tried to go for a carafe instead of a glass each, and his expression clearly implied he thinks I’m a lush).

His follow-up question, “So what do you do on the weekends? Where do you like to go out?” confirmed this. It seemed he was surprised (and relieved) that my idea of a good time is NOT to go out clubbing on Friday and Saturday nights. Obviously, my favorite thing to do is eat and that’s how I spend my time. I’m going to assume that his calling my jacket “mini” was not a way to suggest that maybe I should cut back on my dinners out…

Z was incredibly nerdy in a really endearing way — he wears glasses, has just a tiny bit of pudge, studied math and philosophy at Standford, got a masters in philosophy in London, went to Yale Law School for a year before dropping out, worked at a start-up internet company…and now works for Google. He just moved to Brooklyn and is SO excited to have his own place. (I half ignored the comment about how he can’t wait for his mother to visit so he can buy lots of cool kitchen supplies.) He’s incredibly smart and opinionated. He also happens to work with my mother’s ex-boyfriend, who I guess is dubbed “Angry [B]” at work. (Sad.)

At the end of our date, he walked me to the subway (saying, you’re not going to take a cab, are you? which is exactly what I was planning to do…but then felt guilty about it). I apologized for the time crunch but he assured me that he didn’t mind at all. Which I took to mean that he was obviously bored the whole time.

BUT last night he texted to ask me out again…so I guess it wasn’t all that bad. Can you guess what he proposed as one date idea (along with dinner/drinks)? BOARD GAMES. That’s right. I actually kind of love it, but I’m not sure I like him as more than a friend. Would it be wrong to try and set him up with one of my single girlfriends?!

>OCI Friday Leaderboard: Sept 10

14 Sep

>Yes this one is a little behind but since we have TWO more days to bring in the rear, it seems fair and urgent to make up for last weeks leaderboard/REMINDERS:


KT: 5
KG: 4
KP: 3
CFH: 3*
MB: 2

* waiting for an official post about this third date before it goes in the books forever.


KT: 2
KG: 0
KP: 5
CFH: 2
MB: 0

Ok bottom three, you got 48 hours to HURRY THE JUNK UP.

>Wednesday Wake-Up Call: Sept 8

8 Sep

>So this week’s Wednesday Wake-Up Call comes from another featured Mr. Monday. Don’t have time for a longer intro because I have to go back and re-read this knowledge that was just kindly DROPPED…

When asked to guest-star on this blog, I was a little nervous at first. I’m a numbers guy; words aren’t my strong point. I’m REALLY good at writing “Attached, please find the latest version of the quantitative analysis. Please advise.” Beyond that, my writing skills are about as smooth as KG in a lesbian softball coach outfit or a first date kiss with KT.

The direction of this post will be different than that of the first and second posts from fellow XYs to grace this blog. I’m actually going to offer up a couple pieces of advice on dating for women. Yes, I am that brazen/stupid. Yes, I have a few years of dating experience under my belt in NYC (more than a couple, less than countless). No, I never tried speed dating or online dating. Yes, I currently have a girlfriend. She is amazing.

Now that we got that long-winded-yet-important introduction out of the way, its time to make like Tracy Jordan and drop some truth bombs. It’s what I do.

1. Be Direct & Honest.
Lying sucks. If you lie to get a date (or ON a date) and “pretend” to like something, you’re doing yourself a disservice, and doing him a disservice. Think about it. You’re misrepresenting yourself in a situation where you’re supposed to be getting to know one another. Honesty is refreshing. Why hide anything? Do you still comb the hair on your collection of My Little Ponies? ROCK that. Do you love to scarf down a pound of prosciutto after a night of drinking? SCARF Away. Do you turn on every single light in your apartment when you get a glass of water at night because you’re still scared of monsters? AWESOME. ME TOO. What’s the worst that can happen? He likes you for you?

2. End It If You’re Not Interested.
I’ve heard the “free dinner” argument, but I’m not buying it (no pun intended). For those economists out there, think Opportunity Cost. Leading someone on is more cruel than telling him you’re not interested. It’s 1,924,203.13 times better to be upfront and honest with someone. It’s science…………. +1 to the people who know who the guy is in that picture.

3. Stop Freaking Out.
If there’s one differentiating (non-physical) trait between a girl and a guy, I would say it’s thought process. Girls think waaay too much into waaay too many things from waaay too many angles. Guys are comparatively neanderthalic. A short list of things most girls worry about: location, conversation topics, humidity, cuisine, versatility of attire, hair, perception, wine pairing, updating friends, enough but not-too-much make-up, bathroom breaks, placement of the table in the restaurant, kissing, offering to pay, etc……. A complete list of things most guys worry about: button down or t-shirt, not sounding like an idiot. I guarantee that most things that may seem REALLY IMPORTANT are not really that important at all. He’ll like you for you, regardless of whether or not your eye shadow is…. ahhhh who am I kidding I don’t even know how to describe eye shadow.

4. He Is Out There.
It’s true, despite what some naysayers say. Don’t listen to what “can” and “can not” be. Don’t settle for Wesley Snipes. You may have met him already, you may meet him 5 years from now. But he’s out there. And he’s the one.

Hopefully you found these male insights helpful. Look again, your dating life is now diamonds! I’m on a blog.

>Date Recap: Man #1, Dates#1 and #2

3 Sep

Okay, so I should have posted this last week, right after my first date. And certainly before I posted on Man#2 (aka Midwest Man). And on Date #2 with Man#1

But anyway, here goes:

Background –
Met on okcu. He’s 31, has a masters in classical music composition, lived in one of my favorite cities (Portland, OR), is tall, hipster-y, lives in Bushwick. He’s currently in a band, teaches music, and sells real estate. Oh, and his initials are BJ. For real.

Date #1–
Long story short, it was fine. He’s nice/smart/cute but….eh. He told me that he used to be a drug dealer (TMI for a first date!). I thought he was gay for the first five minutes of our date, which is obviously not a good sign. I paid for the second round of drinks, which was more than twice as much as the first round. The conversation was easy, but I really didn’t feel too many romantic sparks. I made a point to kiss him on the cheek so he couldn’t kiss me goodnight. I could see him as a friend?

Date #2 –
I started to post about this Wednesday, and now I feel like a bi-atch. Yes, he did pick a terrible lunch spot. Yes, it was cheap and my stomach is still grumbling from the bad sushi. Yes, he let me pay for half (it was $20! And we split the first date. I really think he could have paid). On the upside, he’s incredibly sweet. He skipped out of work to hang out, told me he thinks I’m awesome/smart/fun/pretty in a non-awkward way. And he said he’d give me guitar lessons for free…

In the end, I ducked out a bit early and made sure he couldn’t kiss me. It was daytime, after all. I like his company, but not really interested in more than a guitar lesson or two. Meaning, I probably shouldn’t see him again.

>Lunch with DR

2 Sep

>I don’t mean to beat a dead horse, since I am no longer (nor ever was, really) interested in this friend of mine. But I was so mortified when he shot me down the other week that I just want y’all to know that he has been sending very mixed signals for months.

Case in point:

He leaves work today to grab lunch with me. I meet him in a glasses store. He milks the fact that everyone thinks we’re bf/gf and calls me “hon” a number of times. He slides his foot over so that it’s practically on top of mine. He finds a million reasons to touch my arm/back within the first three minutes of meeting up. When he says hello / goodbye, he gives me a kiss on the cheek and always puts his hand in that intimate spot on the small of my back for a couple moments too long.

I know, I know – I’m reading into everything. And I really, truly am NOT interested in dating him. So that’s it — no more posts on this guy. I’m over it.

>Wednesday Wake-Up Call: Sept 1

1 Sep

>Ok so Mister Monday strikes back. But now, on Wednesday.

Understandably, the only wake up call any of us are REALLY looking for on a Weds is not from an effing blog. But given our current status, we gotta hear how it is from the boys.

Here at SD we’re keeping the guy advice coming so that we can all make it to that place where we actually wake up with a real man. Until then, enjoy your Wednesday Wake-Up Call from the boys’ club.

Last week, our Mister Monday told us about how other girls in the city are bringing the heat via online dating.* This week’s Mr. Monday recounts his first date in NYC:

As a recent transplant to NYC, I thought I would bring an outside perspective and share a recent dating experience of my own…

The background: I have been in the City for 3 months now and was/am simply looking for someone fun and similar to hang with.

The set-up: We were introduced through a mutual friend via email and had written back-and-forth a couple of times to warm up to each other and figure out a time/place to meet up.

The attire: Yes ladies, guys do care how they look and dress. Some, I have noticed (especially in NYC), take it way too far. I decided to go casual with jeans and a t-shirt. I didn’t want to look like I was trying too hard. I did have gel in my hair.

The venue: We ended up meeting at a bar. Some may say “real classy,” but I thought it was really a great place for a first encounter. If the conversation got boring, I could either drink myself into a good time or at least look interested, but distract myself by watching the football game (while continuing to drink of course).

The rundown: Despite my skepticism, it went surprisingly well. The conversation flowed all night; we had a lot in common and shared some laughs. I tried to pace my drinking so I didn’t come off as too much of a drunk, at least right away. I admit toward the end I couldn’t contain myself and ended up having one more beer. When the tab arrived it was a whopping $15…amazing. Salads don’t even cost $15 in New York. Being old fashioned and the gentlemen that I am, I decided to pick up the tab. When I asked the waitress on the way out the door if it was happy hour, she replied with a wink “it’s Anna-hour.” Sorry getting a little off track but thought I would share.

The departure: I could tell from how smoothly the night went that it wasn’t going to get emotional and weird. It was a pretty painless goodbye with a simple “I had a nice time” and “it was great to meet you, hope to meet up again soon.”

Nice, I got the teaser for round two!!

The recap: Overall, Paul has potential. Yes…Paul. All and all, my first NYC “man-date” went well.

No ladies, I’m not looking for romance…but when you are feeling down and out about finding Mr. Right (or even a guy that resembles him) remember that you are not alone.

It is even hard for US GUYS to wade through the d-bags and Jersey boys to find a good friend in the Big Apple.

— Mister MANday (via Wednesday Wake-Up Call)

OK. So this week’s man was looking for Bromance vs. Romance, but I think the lesson is clear:

If boys can put that much setup and energy into a “man-date,” there aint no way we can settle for anything less from a real-date. Forget asking about what you do for fun, or disasterous ex-es, maybe our new line should be, “when was your last man-date?”

* Last week’s Mister Monday, still available, and has yet to follow up on any of the dates.

** This week’s Mr. MAN just moved across the coast for a beautiful girl (cue the “awwww” sound).

For any romance or bro-mance suggestions for either, or to be a future guy guest blogger, hit us up at: sixteendates (at)

>Second date with date #1

1 Sep

>I’m about to go on date #2 with date #1…and I don’t really want to.

Mostly because he suggested we get lunch at Sushi Lounge on St Marks. They have good lunch specials, sure, but a-that place is dirty and b-it’s on St Marks. Gross. I want to suggest another place, but I already picked all the places on our first date so that would be a bit much. I can already tell that there will be no date #3.

(But hey, this way I’m on the repeats leaderboard.)

>Date Recap: CFH Date #2

31 Aug

>How we met:
M and I know each other through a mutual friend. We’ve met in the past but never really hung out one on one. We found each other on okcu (“research” on both our parts) and decided to get a drink.

About him:
M is a radio producer in his late 20s, lives in Clinton Hill. Handsome, charming, smart. He also always seems to be dating someone new.

Since M was sent the link to this blog by our friend (NOT by me, ladies!), I can’t say much. He promised not to read it, but if I were in his shoes I would probably read it anyway…so…I’ll just say that for some reason I was dreading it, but ended up having a really lovely time. I’m looking forward to round 2, which will hopefully involve tequila. (Because he’s a fan, not because I’m an alcoholic).

Now, for the funniest part of the evening:

Towards the end of the night, he admitted that he’d read our blog and had a confession. I’m blushing, of course, because boys aren’t supposed to read any of this shit. And, a confession?! That doesn’t sound good. Has he read my embarrassing posts and decided there’s no chance he’ll ever be seen with me again? Did he ask me out just to get my numbers up, because he noticed I was trailing on the leaderboard? (I was on vacation! And joined late!, I’m thinking.)

No. He was reading through the blog and realized that he is Midwest Man. Yes, that’s right – of KP Date #3 and possible booty call fame.

I mean, really?!?! Really. Just my luck. Does our rendez-vous even count as Date #2, given our no recycling policy? Comments, please.


30 Aug

>A couple things:

1. I know I owe a recap of date #1. Coming soon. And, I may be on the repeats leaderboard this week as well.

2. Date #2 is a friend of a friend, and just happens to have been sent this blog’s URL by our mutual friend. So…I will not be posting very much about said date. (Why does he know about the blog, you ask? B/c we found each other on okcu, which I explained by saying that I have a dating blog. When he asked our friend about this, she said, “Oh no, Christina doesn’t have a blog!” And then I sent her the note a few days later about it, so she forwarded it along, etc. etc. Yes, it is (maybe more than just) mildly embarrassing. So if you’re reading this, M — Hey, I’ll see you tonight.

>OCI FRIDAY: Aug 27 (Addendum)

27 Aug

>CFH is officially on the leader board and no longer rocking double zeros (p.s. there is a whole long conversation thread online about why athletes wear double zero. But, like our blog, is painful to anyone who isnt us/doesn’t care so I decided not to post).

However the offer/slight demand to out our speed dating and have 2 lucky ladies be the new KG and KT come monday night….

Oh yeah, and CFH, we need a recap. As you can see, jobs are not an acceptable excuse.


27 Aug

>Crap. It’s friday. Crap, its time for the leader board.

Well breaking Sixteen Dates history, KT is the first to date her way over the finish line!!

KT – 4!!!!
KP – 3
KG – 3
MB – 2
CFH – 0


KP – 5?!?! (ok, everyone give your VS free panty mail coupons to KP)
KT – 1
KG – 0
MB – 0
CFH – 0

Also, given the fact that CFH is rockin the double zeros and no longer globe trotting and fraternizing in Canadia, it’s time for some drastic measures.

When signing up for the date-a-palooza, we got an additional speed dating event coming up THIS monday. What does that mean? It means that CFH and one of your other lucky ladies should go as KT and KG to the event to catch up with KT at the victory line.

Who’s the lucky other taker??

>Oh No

26 Aug

>More to come later.

However – Currently in a client meeting (15 of them + about 10 Colleagues) – and they’ve asked if i can show the blog at the lunch break.

just sayin’


>Update on #3 & #4

24 Aug

>Congrats KT on being the first to cross the finish line. Well deserved win!

Now you must cheer the rest of us as we hobble across the line.

Ok so working on dates three and four. So far date number three is looking like it’s going to be a set up by JB and SP. SP has been trying to get me on date with this guy for quite some time. Now what she’s introduced him to JB and JB has approved – they’re now teaming up against me. He’s a fabulous man, good looking, solid job, very funny, charismatic etc and I know this would be an absolutely fun date. However in typical girl fashion – There is a MAJOR character trait that I cannot overcome. So big deal right – its just a date, it just gets me closer to to the finish line – its not like I’m going to marry the guy – right?

Date #4 – I feel like date #4 is going to have to be via online dating. I have yet to tread the waters of the OK Cupids/’s and the like – so I feel like I owe the blog and men of these various communities a once over. It also helps that Mr. Monday posted about this yesterday and removed a lil bit of the insecurity of how to guide myself through all this – so we’ll see. I have no doubt that I can provide a response more witty than “everything is bigger in Texas”.

I just need to remind myself that this can’t be worse than broken locks or bugs!


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