Jess, I "had" one of those. It helped meeting her and sizing up the competition, so to speak. It's an irrational feeling, so don't count on being able to rationalize it away. You may have to figure out how to put yourself in a situation where you feel more confident. It won't happen in an athletic setting, but meeting her in a social setting might, with your boyfriend.
Winter riding is much less about badassery and much more about bundle-uppery. - malkin
1995 Kona Cinder Cone commuterFrankenbike/Selle Italia SLR Lady Gel Flow
2008 white Nakamura Summit Custom mtb/Terry Falcon X
2000 Schwinn Fastback Comp road bike/Specialized Jett