2. Ask to Borrow a Pen

Level of Success: 50%
Level of Courage Needed: 7 of 10
Bring a crossword or even just your agenda, day planner, or notepad. Rifle through your handbag, then get up the courage to smile brilliantly and ask him if he has a pencil or a pen. Chances are, he will, and will be more than happy to share with you. Use it to write a quick note or fill in a word, then put your notebook away and return the pen, thanking him gracefully. Say something like, “Thank you so much! You’re such a lifesaver!” If he’s interested, he’ll use this as a segue to begin a more meaningful conversation. If he just takes the pen back with a nonchalant, mumbled “No problem,” move on. He’s cute, but not at all clever.

Photo Credit: biffybeans