Category Archives: awkward times

Revisiting old territory

This blog is back in town.

Kinda.  I’m going to try.

I’ve been thinking about writing this post for a few weeks.  Honestly, I’ve been thinking about writing this post for a few months. I knew that entering a year-long master’s program while working full time would be busy, but I never could have anticipated how much of a life-suck it would be, leaving me with no time to shave my legs except once every two weeks—let alone indulge in the luxury of writing blog posts about my love life.  (Which, minus one colossal failure of a non-relationship relationship—typical—has been more like a love-less life as of late.)

I’m still doing the whole master’s/full-time job thing, but now I can see the light at the end of the tunnel.  In other words, whether it’s because this hell-year will be over in a month in a half or because it’s May and my primitive side is waking up for mating season (as Robert Frost put it, “spring is the mischief in me”…though I doubt he would have given that phrase the same connotation I do), I want to get back on the (dating) horse.  I’ve stumbled upon a little more free time, and suddenly the businessmen on my bus are cute again instead of annoying obstacles in my daily commute.  Pretending that I am a character on Gossip Girl and that Nate Archibald is my boyfriend is getting old.  I want the real deal, not a romance with WB-17.

What's not to love?

What’s not to love?

But how?  I find myself in a familiar spot: afraid to get back in the game.  Over the past month I have been guilty of the following: 1) Meeting a gorgeous English master’s degree student at a bus stop (who knew stuff like that happened in real life??), having a great conversation on the bus, and then totally chickening out when it got to my stop and I wanted to ask for his number; and 2) Meeting a cute friend-of-a-friend and immediately wanting to have at him but being too freaked out to even friend him on Facebook until days later.  I am lame!  (Slightly less lame or slightly more lame because I posted a missed connection on Craigslist after bailing on my plans for Bus Guy?)  I remember, in a hazy sort of way, a time when I had the guts to ask guys out instead of waiting for them to do the honors—a time when I felt like I had options.  A time when I was…in college.  I know I’ve asked this question before, but how does one meet people in The Real World?  And do so in a way that feels casual and safe and empowering?  Urgh.

So, here I am, back to square one and back to this blog.  Tune in next week for more awkwardness and angst.  In the meantime, wish me luck.


Things I have learned about dating in the Real World

College was this weird little bubble where all of my potential boyfriends were pre-selected for me by a group of counselors in the Admissions Office.  My school was so small that before I got involved with anyone I pretty much knew everything about them through the combined powers of mutual friends and Facebook.  I always felt fairly confident that the guys I had my eye on were okay—they weren’t, I assumed, axe murderers in disguise.  But now that I’m in the Real World of Adulthood, there is no pre-screen for my dates other than Google.  The tiny college town where I knew everyone has been replaced by the much-bigger East Coast city where I barely know anyone.  For the past four weeks, I’ve been trying to figure out where exactly one meets men post-grad.  Here are my findings:

At the bank:
The other day as I’m walking to my new bank to complain about some error they have already made, I run into a group of people promoting Sabra Hummus by giving out free containers of their product along with bags of SunChips.  Considering my less-than-affluent status, I gladly take their offerings.  As I continue on to the bank, I run into yet another Sabra cart, and quickly stuff my first round of samples into my bag so I can collect another round.  (Yes, I am that cheap.  Hey, a girl’s gotta eat.)  Long story short, I enter the bank juggling three bags of chips and a stack of hummus containers.  As I’m waiting in the seating area to talk to someone, this dude who’s grungy but not unattractive and is also waiting there strikes up a conversation with me.  He attempts to make a joke about the huge bowl of complimentary lollipops on the table, asks me if I’m still in school (Whyyyyy do I look so young?  I’m in graduate school, man!), and tells me that he is a pianist (Did he just say he’s a penis?  What?  Oh.  I may be in grad school, but I am still immature).  When his banker comes for him, he gets up and goes to shake my hand, which is embarrassingly difficult because first I have to slowly transfer all of my free food to my non-dominant hand.  So much for smoothness.  Unsurprisingly, he does not ask me for my number.

Crossing the street:
As I’m making my way through the crosswalk, this old and I think homeless guy walks right at me, and I have to change course at the last minute to avoid crashing into him.  “Hellllllo” he says in deep voice.  I proceed to run away.

At bars:
Finally, with no success, I begin seeking advice.  “Where do you meet guys?” I ask a friend of mine who has lived in the area for a while, trying desperately not to sound desperate.  “At bars,” she says.  At bars?  I’ve always been kind of wary of that.  I don’t know why—there’s nothing wrong with meeting a guy at a bar.  I guess it’s the part of me that wants to have a really cool story about how I met my guy.  Like, I want to be able to tell people that we did meet randomly at the bank or crossing the street, or because we both reached for the same book at the same time at the bookstore, or because we were both eating alone at a restaurant and decided to share a meal.  I like the idea of meeting someone spontaneously, and somehow meeting a guy at a bar just seems so…expected.  But where, you ask, have I had the best dude turnout?  At bars, of course.  Last Saturday night I accrued two people’s phone numbers and three new Facebook friends, and those individuals were all dudes.  And one of them has been texting me, so it might actually be…promising?  We’ll see.  But you heard it here first: the bar is a den of love.  I especially recommend beer gardens; if your experience is anything like mine, your friend will buy you a huge beer and before you know it you’ll have assembled a clique out of the people you met in the bathroom line.

Bar Mitzvah blues

Before I had gotten my first kiss, I looked up to a friend of mine who was much more experienced than I was.  I would sit for hours, enthralled, while she recounted her boy adventures (yes, that was a Dawson’s Creek reference, thankyouverymuch)—but there was one thing I never understood.  “It just happened,” she’d say, telling me how an innocent hang-out session in a male friend’s basement had become a make-out session.  “It just happened,” when her other friends weren’t looking; “it just happened” between her and the guy she supposedly hated; “it just happened” at school, at the mall, in someone’s car.

I couldn’t fathom, then, how physical encounters progressed from secret desire to reality—and did so naturally, without you having to make a grand declaration or even a small admission of feelings. How could one get from point A (not kissing) to point B (kissing) so smoothly?  It couldn’t be possible!

Of course, I quickly learned the truth of what my friend had said.  Sure, sometimes making moves ends up being pretty awkward, but other times it just happens.  You’re dancing with a dude and then, almost accidentally, his tongue is in your mouth and your friend is giving you a double thumbs-up over his shoulder.  (Um, that happened.)  You’re lying side-by-side on your bed having a nice conversation, but suddenly you’re not talking anymore and things are happening.  Oh, so that’s what she meant.

A few summers ago my family flew across the country for the bar mitzvah of a family friend’s son.  Their much-older son is my age, and at the reception he introduced me to his best friend, who I’ll call Phil.  I didn’t think much of Phil—he seemed like a major bro, and at the time I was trying to avoid guys who appeared too jock-like because I’d had some poor experiences dating athletes in the recent past.  Plus, this was one of those embarrassing occasions when your whole family is around—no time to flirt.

Then—I think because our family friend forced him to out of some bizarre sense of hospitality—Phil invited me and my brother to a party he was hosting at his house that night while his parents were out of town.  Since we had nothing better to do, we agreed to go.  I thought it would be a nice chance to escape the hotel and have a few beers—nothing more.

Flash forward to that night.  We start talking, and Phil doesn’t seem like too much of a bro after all. He majors in Public Health.  And he tells me that he spends his summers volunteering at a clinic in Africa.  He’s the perfect Jewish future-husband of my dreams.  On second thought, I AM IN LOVE WITH HIM.

And then, it just happened.

We were having a conversation, and suddenly he was holding my hand under the table.  (Let’s remember that my younger brother was witnessing this…eeep.  It was definitely a turning point in our siblinghood.)  Then we were kissing in his bedroom.  And yes, he was a good kisser.  Very good.  It was the most fortuitous random hook up of my career—who knew I would meet someone at a bar mitzvah?!

Everyone ended up spending the night (you can imagine the great conversation I had with my brother, who very sweetly and innocently asked, “Where did you sleep last night?”—he had slept in Phil’s sister’s empty room—I assured him that we’d kept it PG-13), which gave me enough time to decide that I really did like Phil, which was unfortunate considering that I was leaving town the next day.  Even my brother agreed that he was a really nice dude.  I felt slightly devastated about the timing of all this, but comforted by the knowledge that I would have good fantasy-fodder for at least another year.  (We could meet again at the next special occasion!)

I won’t pretend that things weren’t awkward at brunch the next morning with the other bar mitzvah guests.  My mother, because she’s my mother, was aware of the situation even without me saying anything.  (When we left she pulled me aside and said, “It was Phil, wasn’t it?”  How does that woman know?)  I hate to say it, but I guess this is one of those stories that just goes to show that you never know where or when you’ll meet someone awesome.  The take home message?  Personally, next time I go to a bar mitzvah, I’ll remember to shave my legs first.

Despicable me

Didn’t I say that I hate it when dudes who I’ve previously been involved with ignore me?  In the past less-than-24-hours these two things have happened:

1) Yesterday on my way to the coffee shop I saw a guy I went out with a few times, we made eye contact, I took out my obviously un-ringing phone, pressed it against my ear, and said “Hello?” to dead air to avoid an awkward conversation-wave-thing with him.

2) This morning as I was finishing my run at the track I saw a guy I went out with several weeks ago and pretended I was so absorbed in my workout that I wasn’t aware of him, continued to avoid eye contact while I was stretching, and then left as quickly as possible.

You guys!  I am a perpetrator of the very behavior I despise!

It’s difficult to navigate the weird territory of having briefly–very briefly–dated someone.  I want to be friendly, but it’s just so damn awkward.  (I mean, I guess it doesn’t have to be, but it is.)  We went out, and then one/both of us decided that that wasn’t worth doing again.  Now what?

Both of the guys I’ve mentioned are really nice, good people, and I don’t have any hard feelings toward them.  We normally say hello when we run into each other, and our interactions are always perfectly polite.  I appreciate the fact that they’re still willing to acknowledge me, unlike so many other dudes I’ve dated.  But then there are times when the idea of interacting with them suddenly feels like the most. uncomfortable. thing. ever.  I don’t know why this happens, but when it does I find that I can’t bring myself to utter a simple “hey.”  And then I feel like an asshole.

BUT!  Is it really so wrong?  If these had been men that I’d been serious with for a long time, I wouldn’t ignore them.  As I’ve written about before, I don’t think it’s very kind to pretend that people you once had feelings for/were intimate with don’t exist.  However, since these particular guys are at acquaintance/casual friend status with me, am I a terrible person for skipping a passing greeting?  Sometimes I just want to walk across campus without having to engage with love interests gone awry.  So sue me.

Besides, there are very few people I would make a point of saying hi to while wearing my workout clothes.  Trust me, it’s not a pretty sight.

Couldn’t have said it better myself

Quote of the week from Woody Allen’s 1996 film Everyone Says I Love You.  Drew Barrymore’s character has just been kissed by a man who recently got out of jail.









Him: How was it?

Her: Uh, very interesting.  I’ve never been kissed by a sociopath before.

Just like in the movies

How come kissing in the movies always requires such odd physical positions?

  1. Vivien Leigh’s neck is about to snap in half and Clark Gable looks like he’s eating her face.
  2. Kate Winslet must have pulled a muscle doing this.
  3. In the rain and upside down?  Pretty hot, not gonna lie–but seriously, how does that work?


My prevailing feeling after my date this week is that DATING. IS. SO. AWKWARD.  Moreover, I. AM. SO. AWKWARD.  Seriously—while I am generally confident in my intelligence (at least when it comes to literature and every single episode of Dawson’s Creek; my father once had to send me talking points about current events when I had a date with a Politics major), meager humor, and ability to carry on a conversation, I am not so sure that I would want to date me.

To be fair to all parties involved, I would not say that the date was a failure.  He scored a point by bravely asking me out in a public place where a lot of other people could hear my potential acceptance/rejection.  I scored a point by getting back on the horse, so to speak, and putting myself back out in the scary, weird, and often creepy world of dating.  We both scored points by coming up with enough stuff to say to each other for an hour and a half.

My problem on dates—and let’s face it, in life in general—is not being able to get out of my own head long enough to just experience my feelings.  Instead, I feel compelled to analyze my emotions and level of attraction throughout the entire thing, such that I spend the whole time engaged in an inner monologue that goes something like this:

Me: Hmm, do I think the face he makes when he laughs is cute?

Me: Yeah, I guess it’s kind of nice.

Me: Wait, nevermind, not that nice.  Yep, I’m definitely not attracted to him at all.

Me: Well, that’s kind of an exaggeration.  I guess he is sort of good looking…

Me: But would I want to take off his clothes?

Me: Sure.  Maybe not.  I DON’T KNOW.

[end scene]

You get the picture.  It is nearly impossible for me to stay in the moment of the actual date rather than planning out what I’m going to report to my friends after the fact.  As a result, I feel kind of stiff when I’m talking to someone, and I think it makes me come off as stressed out, which is no fun for a) me or b) my date.  This time, for example, I was so wrapped up in coming up with interesting questions to ask this guy to keep our chat rolling along smoothly—and he seemed to be doing the same—that it became more of a mutual job interview than a date.  Eeep.

The only good news is that my mental babble often provides a good shorthand for how much I like someone.  Usually, if I don’t find myself questioning how I feel—or if the answers to my mental checklist of Do I find him attractive?  Am I going to say yes if he asks me out again? etc. are all an unequivocal “YES”—then I know that this person is someone I dig.

Unfortunately, it’s a fallible method.  I’ve had awful first dates followed by amazing second dates and amazing first dates followed by awful second dates.  It’s always great when the chemistry is just there, but I’m a firm believer that it can also take some time to grow in.  The question is, how much time?  How long do you wait for the dates to stop feeling awkward and start being awesome?

Comment with answers, if you’ve got ’em!

Five perks of dating at a tiny school in the middle of nowhere

1. He lives in your dorm.  The guy who smashed my heart into a thousand pieces freshman year ended up living on my hall during sophomore spring after he returned from studying abroad.  The first time I saw him was when I was walking out of the co-ed bathroom after a shower.  Wrapped in a towel, with mascara dripping down my cheeks and my hair plastered to my neck.  Welcome back to the good old USA!  We walked by one another without saying a word, and I used the women-only bathroom for the rest of the semester just to be safe.

2. You always see people you know on the walk of shame.  Did that kid you have class with twice a week realize that you were wearing last night’s clothes when he cheerily greeted you as you walked into your dorm?  Yes.  He most definitely did, and he also noticed that your hair is suffering from a bad case of someone-else’s-bed head.

3. You always see people you know when you’re on dates.  There is one coffee shop in this town where a single girl can go for a casual rendezvous, and it’s sure to be full of people you have to say hi to in order to avoid being impolite.  This can range from awkward to excruciatingly uncomfortable for both you and your date (one guy I was with resorted to checking his email on his phone while I got sucked into a ten minute discussion with a professor).  Plus, that barista is totally judging you for coming here with so many different guys in one week.

4. You will know when he starts dating someone else.  You will see them together all the time.  There they are, holding hands on the way to class or having a romantic dinner for two at the cafeteria.  You want her to be uglier than you.  You want her to be less intelligent.  But let’s be honest—she’s probably a double-major with a high GPA, a sexy dancer, and very, very skinny.

5. The remnants of relationships past are everywhere.  There’s that booth in the student café where the two of you had a fight one time.  The spot outside the dining hall where he kissed you.  The place on the quad where you liked to strategically sunbathe in case he walked by.  As a friend of mine put it, ghosts run rampant here.  The good news is that since there really aren’t too many places to go, you’ll likely have a whole new slew of romantic memories in all of the same locations in no time!

Since I like you, I’m going to act like I don’t like you

I recently ran into a friend of mine right after she had encountered a guy who has been flirting with her for the past few weeks.  Watching the two of them interact, it’s obvious that he’s into her: the minute she enters the room he turns all of his attention to her, he never runs out of things to say when they’re talking, he finds a ton of small ways to touch her—and he teases her relentlessly.  Most of the time their banter is a major turn-on, because it shows how quick and witty he is and it always keeps her on her toes thinking of the perfect comeback.  It’s this fun little game that the two of them play together, and it’s exclusively theirs.  Other times, though, it totally sucks.  “Why,” my friend asked when I ran into her, “does he always scowl at me like that?”

It’s the oldest trick in the book, really.  We like people who provoke us, who make us think, who drive us crazy.  According to that great tome of dating advice, Wikipedia, “Challenges (teasing, questions, qualifying, feigned disinterest) serve to increase tension.”  A brief Google search returns literally millions of results with instructions on how to play hard to get. outlines five easy steps: 1) Flirt with your guy like crazy, but make sure that he sees you flirting with other guys, too; 2) Wait a day before calling him back—not too long and not too short, it’s the perfect amount of time to keep him guessing; 3) Only answer his calls and texts every other time—that way, you only appear “partially interested”; 4) If you feel the need to actually ask the victim of your affections on a date, opt for a group outing but never a one-on-one thing.  Step 5, the sneakiest one of all, instructs that you “Tell one of his friends you are interested in him, but tell another friend you don’t want a relationship.  This will send him a mixed message, which ultimately makes you look hard to get.  He won’t know if you are really ‘into’ him or if it’s just a rumor.”

Somehow, I’m not sure that this is the best way to go about wooing Mr. Right.

The implication of this confounding plan seems to be that the harder we have to work to win someone over, the greater the payoff.  It seems ironic, though, that our first recourse when we like someone is to act as though we don’t like them.  How many times have I waited for hours to text back a guy I’m into just so he won’t think that I’ve been obsessively waiting for my phone to vibrate?  How many times have I walked right by a dude I’m crushing on just so he won’t have a clue?  And then, of course, he doesn’t have a clue, and he starts dating someone else!  It’s preposterous!  Yet, I’d be hard-pressed to find someone who’s never done it.  I mean, hey, it worked for this girl, didn’t it?

A while ago, I told myself that I would stop playing these inane and often ill-fated games.  When someone texted me, I would text back right away.  When I saw someone I thought was cute, I would make a point of saying hi.  I always list honesty as one of the things I am most looking for in a relationship, so why not be honest?  (The number of emails I would have sent saying “I miss you” to the current object of my heartache, for one thing…)  The problem is that we’ve all been conditioned not to show interest.  The other day as I was walking to the library I saw a guy that I’ve danced with a few times at parties.  Just some minor flirtation, that’s all.  I looked over to greet him, and he was looking at some imaginary point in the far, far off distance.  It wasn’t that he was pretending not to see me—he was pretending that I wasn’t there at all!  So much for trying to be up front about things.  In a way, I guess, playing hard to get is safer: you never have to admit that something suggestive and potentially embarrassing is going on.  Safer, yes, but it seems to me that both giving and getting compliments could be a lot more fun.

Well, that’s all for now—I’m off to not return a few text messages!

The kiss that is a contract

You’ve been texting for weeks.  You’ve gone out on dates.  It’s clear that you both like each other.  Then there you are, standing so close.  You know what’s about to happen.  Everything is going smoothly.  Well, as smoothly as these things can go, anyway.  Then, before you can stop it: that awkward moment when he asks if he can kiss you.

The first time that this happened to me was, appropriately enough, my first kiss.  It was with a guy who I worked on the high school newspaper with.  We had stayed at school late working on the next issue, and I was driving him home.  (Yes, I was old enough to drive—older in fact—when I got my first kiss.  Late bloomers for the win.)  I pulled up in front of his house and put the car in park so he could get his backpack out of the trunk.  Without warning he turned to me and uttered a variation of what I would go on to hear many, many more times: “So, are we gonna make out now or what?”

I didn’t know what to say.  Everything buzzed.  I had been waiting for this moment basically since I first noticed the opposite sex.  I thought this guy was cool, but I had given up on him ever liking me long ago.  “I don’t know” I answered, “do you think we should?”  And his reply: “Yeah, let’s do it.”  He stuck his tongue in my mouth for about thirty seconds and then pulled away, said “Peace!” and exited the car.  And my life—we barely spoke to each other for the rest of the year, a situation only made worse by the fact that we not only worked on the paper together, but were in the same homeroom and took our own two-person poetry class with a favorite teacher.  Oy vey.

I was swept up in what I then believed to be the passion, the raw lust of this exchange in the front seat of my dad’s Honda Accord, for about three days.  (Read: three months.)  Eventually I realized that the delivery of what he must have thought was a choice one-liner was unequivocally lame.  College boys didn’t do stuff like that, right?  Wrong.  Cut to sophomore year, when a cute senior guy invited me over to his house to share a bottle of wine.  When we finished it, he conveniently offered me a tour of his house, which conveniently ended in his bedroom.  As I was admiring his seashell collection (what? he was very into nature, okay?!), he looked at me and said “Would it be really out of line if I kissed you right now?”  Well, we had just been flirting on his living room couch for two hours.  I looked at the floor.  I looked back at him and he was still looking at me, waiting for a verdict.  I looked away again.

“Um, I guess it wouldn’t be that out of line.”

I hadn’t decided if I wanted the kiss yet, but given that we were already practically in bed and that there was a blizzard outside—I knew I wouldn’t be leaving anytime soon—I was well aware of what was coming.  It’s not that I was opposed to the idea, just that his question had been so awkward.  To be fair, it probably wasn’t awkward to him.  He probably thought it was nice, that he was being a gentleman.  True, true.  And yet.  Something about a guy asking if he can kiss me makes me not want to kiss him.  Shouldn’t I have been appreciative of the fact that this dude asked permission instead of just mauling me on the spot?  Yup.  Isn’t this a sign of politeness, of chivalry?  Totally.  No matter how good the catch, I just can’t muster the will to respond with a simple and direct “Yes.”

It’s not that I want men to presume that they can do anything they want to me.  Theoretically, I like a man who takes the time to make sure that what he wants to do is what I want to do, too.  Sometimes, though, I just want you to kiss me, no questions asked.

Realizing, however, that this seems to be a trend, I’ve been trying to work on my responses.  “I guess” just won’t do, especially if it’s a guy I really like—I don’t want to give the wrong impression.  Unfortunately, this, like anything, takes time.  The last person who asked if he could kiss me was someone I had strong feelings for.  Thinking about how much I wanted to kiss him, I couldn’t sleep at night.  Finally, the moment came after the texts, the dates, the standing close together.  We were lying on my bed, holding hands.  “Can I kiss you?” he asked, sweetly and with his light brown eyes so earnest.  “Yes!” I wanted to shout.  “Yes!  You can definitely kiss me!  Please do!”  But hey, baby steps.  “Uh huh” I said, and leaned in.