Dating Boys. Not Men.

I’m not sure why I have been attracted to younger men, or as I like to refer to them, boys, in the past year or so.  My two longer-term relationships were with boys three and four years younger than me, and now Jacob (Ski Crush or Bad Texter, depending on how you look at it) is a solid five years younger than me.  Does this mean that in a year from now I’ll be going out with guys who are six years younger than me?  Will I forever been doomed to date 21 and 22 year olds?

Anyway, Jacob and his four college friends were sitting at the back table at Christopher’s as I walked over to meet them.  As I sat down, I had to hold back laughter because no one at the table looked a day over 18.  Dating a younger guy is one thing.  Hanging out with his friends is another.  If I judged the guy sitting across from me solely on his baby-fresh skin and long curly hair, I would have estimated a recent high school graduation, not college.  Jacob’s friends had to be at least 21, though, since they showed the waitress their IDs.  They had to be, right?

 

The group had graduated from college this past December or this past June, making the primary topic of conversation include junior year benders, shooting grain alcohol freshman year, graduation feeling like ‘yesterday’, the odd anomaly that they have one married friend, not having credit cards/savings accounts, and the fact that they hated going out in their area (Davis Square) because everyone there was ‘old’ i.e. between the ages of 23 and 25.

One of them asked me if I had just graduated as well, and I just laughed as I responded, “nope”.  I didn’t think it was completely necessary that I divulge exactly when I had graduated (a dramatic six years, as opposed to their six months).  Jacob, knowing full well that I was older, laughed at my response as well.  They were a very fun group, despite being so much younger.  At one point, we all toasted to “not being married,” which was the exact opposite of what my friends and I usually enjoy toasting to (engagements, weddings, and babies).  It was weird.

They were so fun, in fact, that one of Jacob’s friends (the one who Jacob drove down with to visit his girlfriend) took a clear interest in me.  Sitting across from me, he was fun to talk to while the rest of the group discussed favorite jello shot flavors, but I soon realized that he was flirting.  A lot.  I hoped that it was all in my head, and just post traumatic stress from this night.  However, when the evening was over, and we all parted ways, he asked for my phone number.  I said okay, but slyly walked away to ‘get my coat’ and never returned.  His girlfriend was standing no more than 100 feet from us, and his best college friend was clearly interested in me.  What was he going to do with my phone number?  Silly boys.

The Classic Overtexter

This guy immediately contacted me via Facebook when we got off the slopes.  He sent many Facebook messages before asking for my number, and then proceeded to text me all day every day.  It’s rather unfortunate because I liked him a lot.  Enough to convince him to take the two hour drive to Boston tomorrow from his new place in CT to come visit me and hang out.  After a week of constant texting, my interest has been waning.

And, just texting is one thing.  Using emoticons and confusing your with you’re is another!  (Does he forget I am a teacher and grammar is very important?)  Also, I don’t mean to sound sexist here but I strongly believe that the male use of the emoticon is extremely unattractive.  Granted, I use them and I enjoy when my friends send me little smiley/kissy faces, but when it’s a guy I may or may not be interested in, it’s a huge turn off.

Talented texter or not, he will carpool to Boston tomorrow with his friend and stay on that guy’s girlfriend’s couch.  This was only arranged after he asked if my apartment was big enough for him to stay here.  Obviously, I lied and said it was very small and my roommate and her boyfriend were always here, making it feel even smaller… far too small for another person to sleep over!  (My roommate and her boyfriend are here about one night a month, but I couldn’t have this guy I’ve met once plan on sleeping over!  Please!)

I was shocked to hear him admit that he had never been to Boston before.  When I asked why, he replied, “I never had a good enough reason to visit”.  Am I your reason to visit?  We hung out once!  I’m sorry.  He seemed cool in person, but his texting is far too much.  Way way too much too soon, buddy.  Obviously, I’ll hang out with him tomorrow since he is making the effort to come out here.  But, well, I’m not feeling into it anymore.  Shoot.

He COULD Be A Billionaire

A fun reverie I like to get lost in is the idea that since I have not met ‘the one’ yet, he could be anyone. He could be the next president. He could be an astronaut, a doctor, a lawyer, or a teacher. He could be a (very kind and unpretentious) billionaire with a spare apartment on Beacon Hill, extra house on the Cape, and unlimited frequent-flyer miles. He could be 25; he could be 35. Maybe right now he is traveling the world, or maybe right now he is doing laundry around the corner from my apartment. I think of him often and think about what he might be doing at this moment (I know, I know, that’s super crazy… I’m totally crazy).

Today I set up a new retirement plan. Fun fact: I’ll retire in 2050. That’s the coolest year to retire, in my opinion. Right in the smack middle of a century.

Anyway, when I mentioned setting up my fancy retirement package to my father, he got all serious and started talking about the best ways to invest my money and prepare for a successful retirement. I generally have no idea what people are talking about when they discuss investing and finances, but was appreciative of his attempt to help anyway. Jokingly, at the close of the conversation I said, “And dad, just remember, I could end up marrying a billionaire and will never even need this money.” Our conversation continued as follows:

“You will probably meet the man you’ll marry in 2049.”

“DAD! That was uncalled for! I will meet him in 2013!”

“Well, you should plan like you will meet him in 2049.”

“That is not the attitude I need here. Be positive!”

“I’m just being realistic, darling.”

My own father thinks I have 36 years of single-hood ahead of me. At least I’ll have someone to retire with, I suppose.

Happy Blogoversary To Me!

So, I recently let my one month blogoversay pass without notice.  Now, we can’t let that happen.  Blogging is my new favorite extra curricular!  I wanted to take this special occasion to briefly outline why this blog has changed my life for the better…

1. Dating used to be a mission to find a husband.  My expectation of each date was to find a father to my future children and a partner to grow old with.  Perhaps these expectations were too high.  No wonder I was disappointed.  Now, my expectations have changed greatly.  I’m looking for content to write about.  Period.  Expectations lowered.  Expectations met.  All of a sudden, I leave good and bad dates a happy camper because I know I can craft it into a post!  Win for me!
2. When I went on a lacking date pre-blog, I would just let it bother me for a few days.  Now, when I write it down, it gives me an outlet to get the terrible guy out of my head, into my computer, and out on the internet.  It is so cathartic, and I feel so much better after writing the experience down, often getting anger and disappointment off my chest.
3. A lot of the time, once I post, you, my wonderful readers, comment… on how horrible the guy sounded, on how proud of me you are, on how interested you were on my view of the topic, or on how you had a similar experience.  This is a whole new world for me!  My fabulous friends, who I love dearly, are all moving in with, living with, engaged to, or married to their significant others.  Given this background, there isn’t much talk of dating when we all hang out, and it leaves me wanting of a place to discuss one of the main parts of my life.  You, my dear readers, give me that space.  Thank you so much for commenting, discussing, encouraging, agreeing, reposting, and just showing me that I’m not alone in this messed up world of dating.
4. And finally, while not the kindest reason to enjoy blogging, I do like getting my bit of revenge!  Horrific dates leave me with a bad night; I leave them forever immortalized in the written word.  To quote one of my favorite movies, A Knight’s Tale, “I will eviscerate you in fiction. Every pimple, every character flaw. I was naked for a day; you will be naked for eternity.” (And to think, what I write is not fiction!)

Don’t Cha Wish Your Girlfriend Was Hot Like Me?

I’m not the hottest girl.  I’m not unattractive, but I’m certainly not Rachel McAdams or some other super hot woman.  I have kind of crooked teeth and crazy unruly frizzy hair.  I am struggling with posting this story because I feel like I’m going to come across as a conceited asshole.  I just wanted to start off here with saying I don’t think I’m the hottest.  I just had this weird day where a few boys did.  Here we go.

My cousin Josh was visiting Boston from college, so I took him to the best place for a newly 21-year-old frat boy:  a Harpoon brewery tour.  We met his college buddy, Matt, at Harpoon.  Josh had told me the adorable “how they met” story of Matt and his current girlfriend, Alice.  They had been best friends through freshman and sophomore year and now have been together for almost three years. Josh said he was sure they were going to get engaged this summer once they had both graduated.

After the tour, we had time to hang out by the taps and enjoy all the Harpoon varieties (I strongly suggest the chocolate stout).  At some point age was mentioned, and Josh asked Matt how old he thought I was. “You aren’t a day over nineteen,” he said.  “Nice job getting a fake.”

Josh laughed, “Seriously, how old do you think she is?”

“Fine, 21 or 22, max,” Matt said, looking me up and down, expectantly.  At the mention of my ripe old age of 27, Matt started yelling, “No way are you that old!  You are way too hot to be that old!  Are you kidding?  I’d sleep with you in a second, even if you are that old.”

Woah there!  Flattered and disgusted at the same time, I asked, “Don’t you have a girlfriend?”

“Well, yes.  And she’s beautiful.  But she isn’t hot like you.  Jesus, you can’t really be that old.  You are going to marry someone rich.  Hot girls always get the rich guys.  This is crazy.”  Matt went on and on. The more he talked the more I hated him.  What an asshole!  (Also, why does a hot person need to marry a rich person?) It was all very unnecessary and over the top.  The really bad news:  It was 3pm and we were hanging out with this jerk all night.

He hit on me once every ten minutes, to the point that Josh was sick of it and kept texting me about how obnoxious his friend was and how sorry he was to have brought him out.  At the end of the night, we all headed to Grand Canal for some classic dance partying and, sure enough, Matt kept trying to dance with me.  I repeatedly moved his hands off of my hips and waist, and finally said, “Don’t you have a beautiful girlfriend who isn’t here?  Go home!  Stop hitting on me!  Call your girlfriend!”  He turned around and left.  Without even saying goodbye to Josh.  Or closing his tab.

Minutes later, I was back at the bar for another drink.  I was relieved to have gotten rid of that jerk!  A cute guy walked up to the bar next to me.  ‘Yes!  The night is not a total bust!’ I thought.  I toyed with my hair a little and shifted my weight so I was a bit closer to him.  He looked at me, smiled, and said, “You are hotter than my girlfriend.”  WHAT!  What was going on?  I was in the twilight zone or something!

“What?  Where is she?”

“Oh, she is here,” he frowned, “I am avoiding her right now, actually.  She keeps following me around and wanting to dance.  Do you want to dance with me?”

Appalled, I suggested, “Maybe if you really don’t like her, you should stop dating her and let her down easily before anyone’s feelings get hurt?” A cute brunette in jeans and a sparkly top walked past me, up to him, and gave him a big kiss.  Poor girl.

So, that was how this song got stuck in my head for a few days.  You can’t really blame me.

Not Much of a Stir

A new member of match.com, I was excited to attend my first Stir event. Match hosts these events so people on match can grab a drink and meet person, instead of clicking through pictures and profiles.  I really hate online dating, and am much better at meeting people in bars, so was thrilled to hear about these events.  I anticipated a room full of hot single guys (including my future husband) and nice single girls (including a new host of single girlfriends).  My expectations were clearly too high.

My game plan was to find another girl who came to the event alone, make a friend, and then, together, find some hot boyfriends, while avoiding the creeps.  Well, my plan was immediately thwarted when I realized that I was the only person who arrived to the event alone.  All the girls were in groups of two and three, and I made a few fruitless laps around the bar searching for another friendless girl, while avoiding the many awkward-looking guys.  I never got the ‘bring a friend’ memo, and even if I did, all of my friends are married or about to get married.  I resorted to approaching a pair of girls sitting on some couches and we got to chatting about how weird the event was so far.

The overall vibe was one of awkwardness and extreme discomfort. I hate to be superficial here, but 99% of the guys there were unattractive.   They were all the ones you avoid at bars.  That guy in the corner with the creepy grin, awkward fruity cocktail, and turtleneck sweater who licks his lips every two minutes – he was there.  That other guy in the suit and tie who clearly thinks he owns the place but is actually annoying and overbearing – he was there.  The men with the pedophile mustaches and limps – all there.

Most of the guys there looked like this.

          At one point, three terrible guys were trying to talk to us at once.  Upon learning of my profession, one of them asked when my students grow out of Autism.  Another explained how he thought it would be way cooler to be autistic because you would be super smart, like Rain Man.  The third randomly described his last relationship in painful detail.  It felt like three terrible bad dates at once.  My body language could not have been more clear.  I was sitting in a way that practically had my back to all three of them, and they did not get the hint.  My new girlfriends and I eventually finished our drinks and B-lined it to the bar to get away from them.

At the bar, we met Brett, who asked how long the three of us girls had known each other.  We each responded at the same time with a different lie – since grade school, since high school and since college.  It was a funny ice breaker and a good way to start talking to the only mildly attractive guy in the room.  The other girls eventually left and Brett and I hung out for the rest of the night.  We played a thrilling game of guess my name and split a pizza (and by split I mean he had two slices and I had four).  We also soon realized that we had both attended the same college for undergrad and grad school, both practiced yoga, and were both math teachers.  Clearly, I was into him.

As he left, he asked for my number and asked to hang out.  Unfortunately, this was a week ago, and he has yet to use my number or ask me to hang out.  I guess he was just another flakey one.

That Magical Feeling…

Ah, that magical feeling when you defriend an ex on Facebook.  Seriously, it’s the best.  I should get more boyfriends to dump me so I get the privilege of defriending them.  It’s kind of like saying, “Yeah, I was planning on dumping you that same night you dumped me… you just beat me to it.” Right?

I spent the entire summer posting and commenting on stuff on facebook just so my ex could go on and see how much fun I was having and how wonderful my life was without him.  I’m sure he spent all his free time stalking my Facebook profile crying about how sad he was without me.  Definitely.

I defriended him two months into my next relationship, when I finally felt like I was 100% over him and didn’t need him to see how much fun I was having with my new boy.  Today, I defriended that boy just because.  Because I really am having so much fun and don’t care if he knows it or not.  Because there are a billion other fish in the sea and I can let these stupid ones go forever.  Because I’m happy without him.  I’m happy without both of them.

But it would be cool if one of them called me up and begged me to get back together with him… just so I can quote Taylor (again) and tell them that we are never ever getting back together.  Like ever.

Crushing

 

It feels like I have not had a crush in years.  Wanting to make out with someone I just met at a bar… not a crush.  Enjoying (or not enjoying) someone’s company on a date… not a crush.  I would define a crush as liking someone you hang out with and not really knowing if they like you too.  I don’t hang out with guys unless I’m at a bar hitting on them or on a date.  So, crushes are not too commonplace for me.

 

 

This new crush of mine is (unfortunately) exactly my type.  He is four years younger than me and moving to Connecticut tomorrow.  For whatever reason, this seems to be ‘my type’ right now.  In the past year, I’ve tended to like younger guys or guys who are about to move away.  Both characteristics are quite inconvenient, and yet this new crush, Jacob, fits both.  Why these two stupid traits are usually evident in boys I really like, I have no idea.  And, frankly, I wish I could start liking men who are ready to stick around.

 

 

In this case, anyway, it was great just meeting someone naturally (he’s my cousin’s friend from college) and actually hanging out with someone (we went skiing all day) instead of forcing the ‘get to know you’ phase on a date.  We rode the ski lift up and flew down the mountain together for a few runs and actually, ohmigoodness, got to know each other naturally.  It was awesome!  To me, dates usually feel like two hour interviews where I need to show my date how witty, intelligent, kind, and attractive I am, all while still sizing up his intelligence, sense of humor, kindness and attractiveness and deciding if I even like him at all.

 

 

When Jacob and I hung out, it was just that – hanging out.  I wasn’t trying to impress him and soon I realized that I was very comfortable around him.  He made me feel able to be myself and enjoy his company.  He teased me and complimented me at the same time.  He offered his help and asked for mine, all while demonstrating his overall kind persona.   I found myself extremely attracted to his personality, and for once, it wasn’t his physical appearance that caused the initial attraction.  It was his smile and personality.  It was how he made me feel when I was around him.

 

 

Well, he is moving into a new apartment tomorrow, literally, and will be living a solid three hours from me.  He is also way too young for me, so I guess that’s that.  However, we did make plans to go rock climbing in April and maybe ski again in February.  It feels nice to have a little crush… even though it probably won’t go anywhere.

 

 

The Toll It Takes

Bad dates suck. Worse than a hang over, they leave me feeling sick and lethargic for days. They remind me how blessed I am to have a plethora of friends who are kind, normal, intelligent, caring, thoughtful, and… well… not crazy (like most of my dates have been recently).

Eric was a promising date. I mean, I had at least met him before (unlike online dating). The trouble with Eric was that he didn’t seem crazy at first. He was into traveling, music, wine, and yoga. All good things. The date turned terrible when he started asking about what I was looking for (as in relationship vs. no relationship). I expressed interest in settling down and finding something serious.

Our wine and cheese spread

His response: “Well, you are wrong there. If you are looking for a relationship you will never find one. Relationships just happen. Like when you are walking in a CVS, you will meet someone. But only if you are not looking. Looking for a relationship just screams desperate and men can smell that. You are the only reason you’re single. The second you can be happy with your life, you’ll find someone. Wanting a relationship is like admitting to the world you are not happy and you probably never will be happy. So you get married and have kids? You’ll still be unhappy and alone.”

I shouldn’t have let it bother me, but it did. I can’t get it out of my head and it makes me a little nauseous. I can take a bad date when the guy isn’t attractive or funny, or when he talks too much, but when the man sitting across the table from me degrades something I want, it’s just too much. I mean, we were on a date. Why was it so shocking, strange, and seemingly wrong to be looking for a relationship?

Attracted to Travelers

To quote Samantha, a coworker and good friend, ‘Of course this would happen to you.  Of all people, you would meet a great guy who is going to Africa on Tuesday.  I’m not that surprised.’

I get it.  It’s really funny that I always fall for guys right before they spend six months traveling around the world.  From an outsider’s point of view, it’s hilarious.  For me, though, it’s really damn difficult.  I don’t understand why I can find so many douchbags, assholes, flakes, losers, and jerks staying in Boston for prolonged periods of time.  Whenever I find someone who is NOT a total reject, I meet him two years into the planning of his once-in-a-lifetime journey around the world.  Who the hell has that kind of bad luck?  Oh yeah… me.

This isn’t the first time it’s happened.  Just a year ago I started seeing someone who knew he would be living abroad from July to January.  He led me to believe that I’d go visit him and we’d stay together through his travels…until June.  Then he came clean.  I was just a fun time between his real life and his long vacation.  He stopped his car insurance, settled up with the bank, finished things up at work, moved out of his apartment, and dumped me, all in one getting-ready-to-leave-swoop.

I guess I should step away from my pity party for a moment and explain what Dave did to make last night (or what would make any date, really) so great:

1. holding the door (even the revolving door, which was awkward but cute)
2. picking me up/dropping me off (I hate driving.)
3. rocking adorable scruff (Clean shaven is so corporate.)
4. asking me about my life and listening to my answers
5. remembering what I like to do and making our date involve that (We talked about how much I like art during our first date, and he picked the MFA as the location for our second date.)
6. sharing common core beliefs and values about the world (We both think that traveling, family, faith, and stepping out of our comfort zone are important.)
7. agreeing to disagree and enjoying the debate (He doesn’t like cubism or abstract art and I love it.)
8. alluding to times we will hang out again (even though he was referring to dates 7-8 months in the future)

Samantha pointed out that perhaps I only really liked him so much because there was no stress involved.  I knew that he was about to fly away, so hanging out with him didn’t leave me wondering when we would see each other again or if he was interested in something serious.  I knew the answers – not for a long time, and no.  It did take a lot of the pressure off.

The question I have been pondering all day, though, is this:  While I know I should feel happy because I met such a nice guy and had three really fun nights with him, why do I actually feel kind of sad?