Rebecca Bates, senior editor, @re.beccabates
The Time and Place: 2005, age 17, Houston, TX
The Object of My Affection: Tall boy with very curly hair who always wore a green hoodie. I only saw him in the hallway, and never actually caught his name.
How It Went Down: I did something that, in hindsight, was a little intense and dorky: I baked him brownies, handed them to him between classes, and asked him to come to my improv show. He gave me a hug! And he came to my show! With his girlfriend.
The Lesson Here: This was, of course, a bit of a letdown…but only a bit. Recognizing that nothing is as embarrassing as you think it will be frees you up to do some really silly, romantic stuff.
Chantal Strasburger, assistant editor, @chantagold
The Time and Place: A month ago, Instagram
The Object of My Affection: A high school friend's roommate who I had been hopelessly crushing on for about three years. He never once gave me the time of day.
How It Went Down: After finally feeling some flirty vibes from him at a party, I was determined to keep the momentum going before he forgot about me. But since he left for a work trip to Detroit the next day and I didn't have his number, I recommended a great BBQ joint in Detroit by direct messaging him an Instagram from the restaurant's page. Then he asked for my number. :)
The Lesson Here: Any excuse is a good excuse to start a conversation—so don't overthink the entry point if it gets you talking.