Yours, Mine, and Ours... Sorta

“So, Mr. T and I met for coffee this weekend and it was great,” I exclaimed, waltzing into the office Monday morning.

“Really?”  The Boss Lady looked intrigued.

“Yeah, you should totally go out with him.” There I go again, trying to pawn guys I date off on my boss. She always says no – something about not wanting to settle for my reject first dates. This was different, though; both The Boss Lady and I matched up with Mr. T at speed dating and he had asked us both out independently. Of course, we hadn’t really discussed the logistics of both of us dating him.

“Actually, do you mind if I go out with him?” Boss Lady asked as she glanced down at her calendar.

Scenes from last season’s Bachelor flashed through my mind. Instantly, I saw both Boss Lady and me standing on a desolate beach somewhere in the South Pacific wearing evening gowns and waiting for Mr. T to walk up with a single rose – he could only choose one of us to be his wife. Caught up in the delightful drama of the daydream, I squeal, “Doooooo it!”

The Boss Lady and I have desks that directly face each other, so I’d say we have a work environment conducive to better-than-average interoffice communications.  I used the ten minutes it takes for our computers to boot up to fill her in on the coffee date with Mr. T. I told her how I really think they will hit it off; he’s smart, funny, artistic and nice. He didn’t get mad at me for being 20 minutes late (theme of my life) and he was interested in outdoorsy stuff. He certainly wasn’t bad looking and I thought he was polite. A nice guy – the kind of guy that wears a nice sweater on a first date; he just might be her soul mate.

Quickly, I grew more excited about her date with Mr. T than my own.

My second date with Mr. T was at Geronimo’s restaurant.  I eagerly asked him if he planned on meeting up with my Boss Lady and he said he did. I started singing her praises and then told him I was now writing for The Patch and while I’d be happy to keep dating, I didn’t expect it to progress very far or very fast. Let me assure you, those kind of conversations are way more awkward than movie stars make them out to be. Even though we’d had a good time, I figured I wouldn’t see much more of Mr. T.  I didn’t mind too much though, because I thought the Boss Lady was going to have a great time with him.  Plus, if I pushed them off the proverbial cliff of love, I’d surely be asked to give a speech at their wedding.

Mr. T and the Boss Lady went out a few times, movies, restaurants, and they both came to a dinner party at my house once, but it wasn’t meant to be.  In our post-dating debrief, Boss Lady and I came to a few important conclusions about our situation:

1)      Dating methods employed on The Bachelor do not translate to real life. Unfortunately.

2)      If you are out on a date with a guy who asks you questions about a friend, the best answer to give him is, “You’ll have to talk to her about it.” Apparently, my sudden and awkward attempt at bowing out of a potential relationship with Mr. T confused him and he sought clarification from Boss Lady.  I’m sure I was the last topic of conversation she was expecting on her date.

3)      Matchmaking is difficult work and best left to the professionals.

The ultimate take-away lesson we learned was: we should never, under any circumstances, ever date the same person at the same time again. Ever. It’s just too much crazy for one guy to handle.