In this case it's would you rather ask to date girl A or girl B? Both are equal on paper (record). If there is an issue with girl A, she's going to embarrass you and come to your house (AmFam) 7 times a year, get drunk, and remind you of your embarrassment. If girl B turns you down, you can move on to the next one in relative peace.
If you are smooth enough(play well) you can get either (win series). If you aren't (play poorly), you will get turned down by both (lose series).
It wouldn't be as though you get nothing because you are too shy (your analogy). You are taking your shot either way
Obviously, the flipside is eliminating the Cubs twice in a row would be extra sweet. But if they lose to the Padres, I would enjoy watching that too.