Sex & the Suburbs: The Dating Game – Part IV

Single and back in Connecticut after a summer away, I’ll admit I was excited to be a part of the Dating Game. Hearing of the Anti-Couric’s success, and bound to one-up RingNation, I set up my Plenty of Fish profile and waited for the emails of potential suitors to flood in. Like RingNation…I waited…and waited.

I sat and wondered “What could the problem be?” Sure, I’m not a model. I’ve shirked gay-law and don’t work out 3 to 5 days a week. But I know who I am, what I look like, and I know those things to be funny, and though chunky, still kinda cute. I went ahead and copied my profile over to as well. The Gay Guru is known for often coloring outside the lines…and Bears are a little closer to your Gay Guru’s “type.” The good people at have made their site mostly free on an every other day basis, so it was certainly no stretch on my budget either.

With the exception of a few passive messages and a delightful chat with a guy from Brazil, after several weeks my optimism began to dim. I wasn’t super proud of my next move. But at the risk of never getting a date again, I’m ready to go full-frontal on the disclosure tip: Dateless, horny and remarkably lazy your Gay Guru cast standards aside, said “Fuck it” and posted in the “m4m” section of Craigslist.

As the e-mails from undesirable horny Hartford area men poured in, one in particular stood out. It was from a seemingly well-put together guy from Springfield, Hartford’s often forgotten sister city to the north. The PrissyBitch would have advised against dating anyone from Massachusetts…ever… but this fellow was my age, type, and had a similar sense of humor. We chatted back and forth and I quickly cast my desire to “hook-up” aside because, quite frankly, I thought we were a match and I liked him. Over the next couple of days the fellow and I texted, emailed, and talked on the phone. There was definitely a spark, so I asked him out and we made a date.

Date night came with dizzying anticipation on my part, until, the night before the date…Masshole canceled! I know! Get this, he sends me a text saying that he had a migraine headache starting and it would probably knock him out for the next couple days. When I apologized and told him I hoped he felt better and to contact me when he wanted to reschedule, he informed me that I “passed the test.” This dulled my anticipation to say the least. Test? Weird, right? Still, I trekked up to Springfield to meet him the next night. He was very cute and just as delightful in person as our prior chats had suggested he would be. (Weird “test” thing aside.)

Soon after arriving at his place, I made what was, apparently, my first mistake…I was a few minutes early and he wasn’t ready yet. He hopped in the shower and while I waited in the living room his roommate came home. I was nervous, so when she came in, and was shocked to see me sitting there and not her roommate, I extended my hand and said, “Hi, I’m Masshole…..I mean, uh, I’m Gay Guru, Masshole’s friend…” It was a silly slip, and I thought nothing of it. On the way to dinner, I confessed my “super-dorky moment.” Apparently he didn’t feel the same way and thought instead that I was a big weirdo. I tried to explain it away as just a nervous slip, but apparently damage was already done as he was convinced I was there to assume his identity and take over his life. Charming.

Dinner conversation consisted of Masshole’s complete surgical history, including but not limited to a detailed account of a “late in life circumcision.” The awe inspiring depth of his speech was intermittently interrupted by his need to answer texts. Of course he apologized for that, but the apology was quickly negated because he kept right on fucking texting.

Enthralled with the charms of Masshole, I barely noticed when the restaurant closed. Shocked, I leaned forward and asked, “What time is it?”

“About nine,” he answered. In what I thought was a relatively quiet voice, I responded, “Really? And they’re closed? Huh, even Bertucci’s is open until eleven.” Perhaps I wasn’t as quiet as I thought, but his eyes bulged and he curtly replied, “OK! CALM DOWN!”

Needless to say, I drove back home to the comforts of Hartford’s suburbs with a notable absence of the warm-fuzzies. Being the type of person that hates to live with doubt, I bit the bullet and texted him. I simply asked, “Did I completely fuck that up?” What happened next shocked me, so brace yourselves, my pets.

Through a series of texts back and forth, he made the following points:

  • “We are two very different people with very different value and belief systems, I think it’s safe to say there isn’t much future between us.”
  • “The impression that I got that you may be a tad too elitist…that you see your self as better than others.”
  • “I was quite frankly embarrassed when you loudly began to spout off about the early closing time within earshot of the waitress.”
  • “You were rather without tact tonight…Courtesy, tact, class and elegance. The big first date four.”

Now, I’ll admit to playing dumb and inviting his tirade, but let’s quickly re-examine, shall we? At dinner, I couldn’t get a word in edgewise as he talked about his dick surgery and every other surgery he’s ever had….yet somehow through this one-sided conversation he managed to get a hold of the intricacies of my value and belief systems. He must be especially insightful.

I’m also struggling to find the courtesy, tact, class and elegance one displays in telling a detailed penis operation story! Or how, when he was the one to proudly proclaimed that he will “only wear Ralph Lauren” and I confessed I was pretty much in Old Navy from head to toe, I’m the elitist?

Ok, I’ll give him the elitist thing, I mean, duh….I’m from Connecticut! I hail from the land of Martha Stewart, drive a European car, and had a prior detailed conversation with him about how I would not date anyone with T-mobile, Boost, Virgin, or Pocket Wireless. But what about any of those things would suggest anything other than a touch of snottiness? In my opinion, you won’t find a snob shopping the clearance rack at Old Navy….you’ll find him at the Ralph Lauren section of Macy’s.

As for “spouting off”…Oh, child. On the rare occasion that your Gay Guru has actually “spouted off,” it can only be described as a performance that would make NeNe from “The Real Housewives of Atlanta” look classy. I’m pretty sure my ex, or at the very least his meddlesome rotting crotch of a hag, will back me up on that.

My darlings, I held out, hoping if nothing else to end the Dating Game series on a high note with a great date, leading into a beautiful fall romance…I wanted to bring you a story of dating inspiration. Alas, I was left with an attack of Masshole-ish proportions.

While I won’t entirely write off all men from Springfield, I will write off the Craigslist m4m section as a place to meet men for anything other than booty. I imagine the same goes for the other Craigslist personals sections as well. I’m not ready to write off Plenty of Fish though, a few friends had some great success with the site.

Wishing you all the best and happy hunting boys and girls!



  1. oh honey, i’m sorry the late life dick surgered masshole was such a complete loser. but i laughed my ass off at this!


  2. You know, when i went into this thinking I’d “take one for the team”, I had something a little more torrid in mind. Oh well, made for great material.


  3. Remember that good old expression from the Casanova archives: “I want to have rampant animal sex with your body hole” Nowadays it seems like language is taking a turn where words hold more definition in the slang than they do in their real roots. Oh, certainly I am guilty of this folly of the vernacular as well!



  4. Pirate, The Gay Guru doesn’t name names darling, and I think after reading that, you can understand why. Thanks for reading! Remember, the Gay Guru is here for you, so if you need help with your stalker situation, write to me for advice at:


  5. loved the reading! As for Masshole…..F–k the prick!….i too had signed up for some “hook up dating thing”…. YEA, NO it didnt work for me either:)


  6. Let me see if I’ve got this right:

    * Pre-date mind-games via text message: classy

    * Dick surgery chat during dinner: tactful

    * Faux-articulate post-date analysis (also via text message) rife with unfounded value judgments and snobbery: classy/tactful

    Were you on a date with Mel Gibson? Come clean, dude.

    Dick surgery chat!? On a first date? And during DINNER!? I’m pretty sure that’s a no-no.

    I mean it’d be one thing if it were sexy flirty semi-dirty dick chat (though it probably would still be out of place during dinner – call me old fashioned). But I’m pretty sure true life penis mutilation anecdotes don’t pass the acceptable first date small talk test. Or any date test for that matter. I can’t see how that’s even remotely appropriate or relevant.

    Then again, maybe that just makes me elitist. I mean I AM from Connecticut.

    Also where did he get that Fox Force Five, er, “First Date Four” list – Courtesy, tact, class and elegance.

    Courtesy, I get.

    Tact? No doubt!

    Class. Well that kinda happens on its own if the first two are in place.

    But elegance? I mean… really? Shit, I’d fail the elegance test every time. I couldn’t even rightly define the word let alone embody it. Hell, I’m not a beauty queen nor piece of fancy flatware.

    It’s safe to say you dodged a bullet with this one.


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