Help Me Wager My Dignity On The Cubs

It's that time of year again! The Cubs are about to face the Washington Nationals and I need help thinking of something to wager against my best friend Johnny, who originally hails from Washington, D.C. but now lives in Los Angeles. Johnny is in his late 30s and by the time the Expos became the Nationals in 2005, he was playing drums in my band Bad Teenage Moustache in New York City. But his parents, originally White Sox fans from the South Side, adopted the Nats as their team, and Johnny went with them in order to keep team allegiances within the family whole.

Johnny and I have wagered in the past. We once had a weight loss competition that I won, in which the loser was to have to play and hour of craps in a dress in Las Vegas. But an unfortunate incident involving pepper spray and a psychopathic bouncer forced me to reconsider his fulfillment of the wager. The poor boy had suffered enough.

Then, just last year, we wagered the Nats vs. Cubs season series. The loser had to dress up as Richard Simmons and attempt to lead aerobics outside of Dodger Stadium when I visited last August. Well, to refresh your memory, the Cubs lost two of three at Wrigley and then heroically won three of four in Washington. I won!

Some of you may remember the little video I put together to document Johnny's jazzercise moves, but it's sooooo worth watching again, and if you haven't seen it, it's an instant classic, only made funnier by the fact that Johnny's work computer's browser was filled with cookies for men's underwear ads from searching for a costume. Here it is!

Hilarious, right? Well, now we need to attempt to top ourselves and we need your help! The bet can't be anything dangerous like dressing in drag and trying to use Curt Schilling's bathroom. It has to be good natured, positive and if possible, baseball related.

The Cubs face the Nationals for 4 games in Chicago beginning Thursday, May 5 and then three in D.C. starting Monday, June 13th. Both teams lead their divisions and look like they could both be playoff-bound. If rotations hold up, Jake Arrieta and Jon Lester will pitch during the Wrigley series so I like my chances of taking three of four at Wrigley. But then again, the Cubs will have to face Max Scherzer and Stephen Strasburg. This year, Johnny and I both root for such excellent teams, we may have to up the ante for the playoffs!

But first things first. Help us top our "Sweating to the Oldies" bet of last year, as we wager our dignity for the love of our favorite baseball teams! What should we bet this year? Please give us suggestions in the comment section. Or if your idea is NSFBCB, email me.