Start with a funny observation, question, or compliment. “Hey, you did a great job on your presentation. How did you decide to take it in that direction?” “I’ve never been to this restaurant before… what do you recommend?” “I can’t get over these Halloween decorations. I feel like I’m in an elementary school classroom… it’s kind of awesome.” Ask follow-up questions. “How long have you been playing baseball for?” “Do you usually go to school dances? I’m always on the fence.” “So what’s the best TV show you’ve watched lately? I just finished one and I’m looking for something new.” Add in your own stories when you can, but keep your crush as the center of the conversation. “That’s so funny, my dog did something like that once. We were eating dinner and he jumped up and just grabbed a bite of chicken right off my fork. We were all in shock, haha. Your dog is probably a little better trained than that, I’m guessing…” “Yeah, the last time I went to a movie was one of those early afternoon showings that are really cheap, and I was the youngest one there by a long shot… saving the money was worth it though. I got an extra large popcorn just to celebrate. Are you a popcorn movie person or like a candy person?” When the conversation starts to wane, change the subject to something easy and natural. “So what are you up to this weekend?” “Do you have class later today too?” “How is your history project coming along?” Say goodbye casually, with one last positive or funny comment. “I’m meeting a friend for lunch, so I’d better get going. Good luck on presenting your project later!” “Well, I should probably not be late to this meeting with my boss, so I’ll see you later!”