Archive for the 'Online Dating' Category


F*ck it, Dude, let’s go bowling. *

Dear Amelia,

Just do me one solid. I cant believe I started off a letter with the word ‘solid.’ I sound like effing George Costanza. Pathetic. Let’s revamp.

Just do me one favor. There, that’s much better. Please tell me you stopped seeing me for a reason OTHER than me kicking your ass at bowling. I know, I know…you talked a ton of crap going into our second, and presumably final, date; while I played the whole “but it’s been seven years since I’ve bowled, you are going to totally emasculate me, yada yada yada” card. And then, after one sub-par comeback game, where you did indeed score higher than me, I thoroughly destroyed you thereafter.

I’d like to think that I didn’t blow a chance with a great girl because my ego got the better of me and I beat her at bowling. If that is the case, we wouldn’t have worked out anyway. It isn’t really in me to do shit like that, and if you expected me to do that, you weren’t the girl I thought you were.

But, since then…nada, nothing, zilch. Even though you told a mutual friend that you, ‘had a blast…can’t wait to hang out again,’ you came up with a few lame excuses the next few times I tried getting together with you (seriously, you can visit your Grandmother ANYTIME – I’m just kidding, that’s not really lame…it’s actually kind of adorable), and as a result I threw out this text, “Ok no worries, let me know if you’d like to hang out again,” or something along those lines. Predictably, I haven’t heard from you since. It’s been two weeks, I doubt that I will.

I don’t think it’s because of the bowling. I think it’s because this was a thing, and because you are a normal human being, you most likely were going on quite a few dates in addition to ours, and simply found someone you liked more. As much as I’d like to, I can’t really begrudge you that. I simply don’t have that bone in my body though, or that gene in my DNA. I don’t know how to properly ‘date.’ You and I went out a couple times, I think it’s safe to say we enjoyed each others company…therefore I have no interest in going on dates with other females. It seems like I’d be doing it under false pretenses. Would I perhaps make out with a girl on a dancefloor whilst inebriated on a Saturday night? Of course I would. But I wouldn’t take her out to dinner that week…I’d rather see what kind of potential there is with you.

I’m pretty sure this area of conversation has come up in previous letters…which just proves this series of letters is pointless, since clearly I’m not learning from my mistakes. Unless of course, this had nothing to do with you dating multiple people at once and finding a better match (see what I did there?), and has everything to do with me making you my biatch at the bowling alley.


The Dude

*The Big Lebowski (this girl and I went bowling…was I going to use another movie?)


Would you like to do this again? With you – wouldn’t have thought so.*

editors note: this is a repost of one of my earliest letters.  i do this for two reasons 1. not many read my blog in the early days (not many still do, but i have a few more readers) 2. i cant stop blowing my nose long enough to write a full post. enjoy!

Dear Shayna,

I want to thank you for making me re-think my internet dating habits: Lesson #1 – Never, ever agree to more than a lunch or a drink for the first face to face meeting, dinners are simply too long, and sometimes really painful.  Like it was with you.  So while you may have cost me about $40 (remember, when you offered to split it I couldn’t take you up on it quickly enough), you also taught me something priceless.

Lesson #2 – Whether it is on purpose or subconsciously, you made me realize that we all sell our selves online.  We project an image of what we think people want to see in our profile, and then enhance that image through emails, online chat and dare I say – even an adult-like phone call. I think everyone does this to a certain degree; I like to think I try my best to show people that I am down to earth, witty, and pretty much the man.  You seemed like a happy-go-lucky, easy to talk to, educated individual.  Well, at least you are educated (I can only presume you didn’t lie about your Master’s Degree).  Turns out you were actually quite miserable.  Upon getting the awkward greeting out of the way, I asked how your day went.  Your response, a terse, “Awful.”  I’ll spare you the details, but it was only downhill from there.

Lesson # 3 – You also taught me to watch what I say.  When I mentioned I was looking for jobs at prep schools, you were curious as to why only private.  My answer, if you recall, was along the lines of, “Well the administrative type job I’m looking for aren’t typically at public schools, I’m not certified to teach at a public school, and I went to a private high school so I know the landscape and think I’d really enjoy that environment again.”  I didn’t realize that was such a snobby comment, because you replied, “Private school kid huh? Aren’t you the privileged one.”  At least that wasn’t 20 minutes into knowing each other.  Oh, wait. Yes it was.

Lesson # 4 – I guess I’m not the only one who has trouble reading signals.  Let’s recap real quick: You barely spoke, and when you did something miserable usually came out; you called me a snob; I scoffed at a second glass of wine and dessert; even though I have always paid on the first date unless the female absolutely insists, as soon as you brought out your plastic I think I tore it from your hands to throw in with mine; oh yeah, I shook your hand goodbye.  Despite all this Shayna, you actually had the gall to send me an email the next day informing me what a blast you had and that you wanted to do it again soon. Suffice it to say, that certainly didn’t happen…and if you couldn’t read that signal, hopefully this letter spells it out a bit clearer.

See you never,


PS – I should tell you that my guess is you were just having a bad day, and that you are probably far cooler and sweeter than you presented yourself on our date.  But first impressions are everything.  Sorry.

*The Office, UK Christmas Special


“some people play hard to get. i play hard to want.” *

Dear Katie,

We went on a few dates this fall, and immediately two things were extremely clear to me: 1. you are a tease and 2. you like to play ‘the game.’  I’ll forgive you for item #1, after all 98% of females I know are teases on some level.  In fact, most of you don’t even know you are doing it consciously so it’s not as if I can actually blame you.  Although next time you are on a THIRD date with someone who buys you an expensive dinner and takes you to a romantic comedy he didn’t want to see (starring Justin effing Long), AND you bring up how much you enjoy a good make out session…don’t act all shocked and awed when he tries to kiss you goodnight.  Ok, now that I’ve got that out of the way, let’s move on to the game…

It’s actually hard for me to describe the game, because not only do I not play it, I don’t even really know how to play it if I wanted to.  Why is that, you might ask?  I don’t even know what the effing game is.  What I do know is that I apparently suck at it.  How do I know this? You told me so.

Before I forget I must thank you for being extremely informative, even if you were kind of a bitch about it.

I promise I wasn't even going to open my mouth...Photo Courtesy of

After the first couple times we went out, I realized that I was definitely into you, and unfortunately I made that too clear.  I did not text/email/call/facebook chat/gchat you 17 times a day, or anything remotely along those lines.  Instead, after it had been a week or so since we hung out I

said, “You know I had a really good time hanging out with you last week, I’d like to take you on more of a date date this weekend…dinner and a movie, or something like that.”  So, we went to dinner and a movie…where the story from the first paragraph about me buying you dinner, you talking about how much you like making out, etc etc, may or may not have happened.

That was the last time we hung out.  It had nothing to do with me being overly-aggressive (in your terms) by trying to kiss you goodnight.  Forwhat it’s worth, I’ll tell you my mindset again – we had been out three times, it was a brightly lit parking lot with other people leaving the movie, all I wanted was to give you a quick kiss on the lips; I wasn’t going to ram my tongue down your throat.  But that wasn’t it, apparently I played my cards too early, you told me.  I made it obvious that I enjoyed your company, simply by telling you that I, in fact, enjoyed your company.  There was no chase in it for you.  I should’ve played hard to get, or something like that.

Anyway, as much as I enjoyed our few dates, I’m glad you told me that; because no offense, I would never want to spend too much time with someone who has that mindset.  I don’t think you are a bad person or anything, like I said before, ‘the game’ just isn’t for me.  I tell people how I feel, not in an overly melodramatic way, but the same rule applies: if I like you, I like you.  I’m going to want to hang out because I enjoy hanging out with you; I’m not going to sit on my hands and pretend I don’t so you somehow like me more.

Of course, if I don’t get laid anytime soon I might have to change my ways.  Kidding, I promise.

Hope you win your next ‘game,’

Player ( get it – like, ‘don’t hate the player hate the game…)

*The Adventures of Ford Fairlane – yup, I quoted an Andrew Dice Clay movie.



that’s like the express lane to the friend zone…what the hell’s the friend zone? *

Dear Cassandra,

We went on a date a couple of weeks and I had a lovely evening…only I’m still not sure it was a date.  I’d like to make this clear in person, or at the very least face to face; wait who am I kidding, no one talks face to face anymore.  I’d like to make this clear via blog/letter (or text message, since you probably won’t read this): I don’t really want to friends.  Really, it’s nothing against you, it’s just that I already have way too many friends.  In fact, I wish I could purge my real friends like I can my facebook friends…unfortunately there is no delete button for life.  Sorry, let me get back to you, and us.

Our first date was about a year ago, it was an awkward date.  We met for a few drinks, had a lame conversation, hugged it out and I thought that would be the end of it.  I’m usually a pretty good conversationalist, and now I know that you are too, but for some reason that night we talked about as well as Brett Favre retires…that is, not very well.  We ran into each other once and had some coffee, and the conversation was slightly better, but I think we were both kind of bored after one mug, and that was it.

I'm not fat + You are as hot as Amy Smart = Perfect couple! Photo courtesy of

I mean, a brief conversation about sports via gchat every once in awhile, but I never thought we’d hang out again.  Then, out of the blue, YOU asked me to meet up for a beer.  I was taken aback, but we had an awesome time!  Granted, we connected over sharing awful date experiences, but we were both laughing and smiling like we’d hit it off.  Again, we hugged it out and promised each other it wouldn’t be ten months before hanging out again.. Ten months, less than ten days later you asked me out to dinner…on an effing Saturday night (ok I guess the day was my choice, but you were totally into it)!  That was a date – we met, I even told you how beautiful you looked, grabbed a drink at a bar, then went to a relatively fancy restaurant (cloth, not paper napkins) and had more great conversation.  Only this time instead about other awful people we dated, we talked about ourselves.  A hug, and a light peck on the cheek later, we went our separate ways.

And I totally might be jumping to conclusions, but based on your wanting to meet up for coffee sometime soon (as opposed to dinner or drinks again), I’m guessing you just want to be friends.  Now let me make something clear: I am not head over heals about you, yet.  I did not get all giddy and call up a dozen friends telling them about some great new girl I went out with.  So I don’t want you thinking I’m on some kind of level you are totally not on.  However, like I said from the beginning…I don’t want to be friends.  If we hang out again, I’d be coming from the angle of trying to see if a romantic type (read: where we get to make out) relationship MIGHT work.  You and I are not headed for the friend zone.  If you aren’t ok with that, I completely understand.  There are lots of reasons you might not want to pursue that kind of relationship with me; none of them are good reasons of course (sarcasm), but that’s cool with me.

Make sense? Good. Sincerely,

Not Fat Ryan Reynolds

* Just Friends (not a great movie, but the quote works)

Letters sent…

December 2012
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