The 1985 Bears Ruined My Saturday Night

Sean FlanneryContributor ISeptember 26, 2009

26 Jan 1986: The Chicago Bears celebrate after defensive lineman William Perry scores a touchdown during Super Bowl XX against the New England Patriots at the Superdome in New Orleans, Louisiana. The Bears won the game, 46-10.

This is a photo of me at a BBQ this weekend, wearing a 1985 Super Bowl Champion Bears tee shirt:

At a bar, later that night, that shirt was responsible for the most awkward moment of my life.

(Quick Background: I am from Cleveland originally and follow the Browns passionately, but, in the 1980s, when I was growing up, my second favorite team was the Chicago Bears. I now live in Chicago, but have not followed the Bears closely over the last few years—only the Browns). 

The situation:

A women who looked, at most my age, yet in all likelihood younger, approached me—

WOMAN: "I just wanted you to know: I love your shirt! And I wanted to say, I was at this bar when I watched that game!"

I was amazed. Here’s this woman, who I thought to be at most 28, telling me that she was old enough to have a beer in a bar in 1985.

ME: "Wow. You’ve aged really well."

CONFESSION: that is an atrocious response to an opening line, by a woman. However, I was recovering from the single most inaccurate age guess of my life (at the time) and all social abilities flew out the window, in a confused rush.

WOMAN: "Yeah, sure." (said in mock encouragement)

She then passes a dismayed "can you believe this guy" look to her friend.


• This woman thinks my shirt is for the 2007 Bears team (that lost the Super Bowl to the Colts). NOT the 1985 team.

• She has never heard of the 1985 team.

• It never occurs to me that she’s talking about the 2007 team.

Thus, she thinks I’m congratulating her on aging from an event that happened less than three years ago. I think we’re talking about the year 1985 and am speaking oddly nostalgic.

She rolls her eyes again.

I start to wonder why she’s so mad about a compliment on her aging. Even if it was stated a little awkwardly, it was sincere.

That’s when it hits me: "she thinks I’m hitting on her!"

...This, of course, is all wrong. She does not think I’m hitting on her. She just thinks I’m crazy for talking about the year 2007 this way...

Also NOTE: through a series of unrelated misunderstandings, I incorrectly believe this woman is my buddy’s boss.

Thus, I feel obligated to ‘clean up’ this misunderstanding and am refusing to just shut up and walk away, until I feel the conversation has turned positive...

ME: "You know, I really meant that: you’ve aged great."

Her jaw nearly drops.

WOMAN: "What??"

ME: "Come on you must know that...You know, not every thing a man says is a line."

I start scratching my temple, during these final points, so she will see my wedding ring. I think this will further assure her that I am not flirting.

ME: "Some things are just facts. Some people age really well and you happen to be one of them."

Now she just looks confused...I am talking about the year 2007 like I have been in a space ship and do not understand how humans have aged.

Her friend walks over and joins us. He points to me.

FRIEND: "Oh, great shirt man."

He looks as young as her. He then turns to her.

FRIEND: "We saw that game here, remember?"

Jesus...there are two of them!

FRIEND: "Where did you see it?" (to me)

ME: "At my best friend’s sleep over."

They now think they are talking to the weirdest man on Earth. A full grown man who still introduces people as "his best friend in the world" and says "sleeping over" rather than "crashing on a couch."

Even I am starting to detect the strangeness. Everyone is glancing at each other with squinted, confused eyes, as though to say, "Do you have any idea what’s going on here?"

Luckily her friend then adds, almost in a near panic to change the topic:

FRIEND: "Rex Grossman really shit the bed in that one."

Oh my God. They are talking about 2007. Worst yet, they think I’ve been talking about 2007, when, in fact, I’ve been talking about fourth grade.

Screw it. I just gotta get out of here. I’ll probably just make things more confusing if I try to explain the difference between the two Super Bowls to these guys.

ME: "I have to go find my best friend."

And I walked away.

I told my wife the story when I arrived home. "God you’re awkward with women," she said "it could not have happened to any one else."

She blames my awkwardness. I blame America’s inability to read Roman numerals. If the NFL just started using regular numbers for the Super Bowl (like every other company on Earth that releases more than five versions of a product), all of this could be avoided.

NOTE TO DISCOVERY CHANNEL: if you switch the numbering system for "Puppy Bowl" to standard Arabic numbers (rather than Roman numerals), I will immediately consider you to be the most relevant game on that day.

(this offer also extends to Budweiser, should they choose to restart "Bud Bowl", without Roman numerals)


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