Gauge his interest with an open-ended question. “It’s been fun working with you in our group project. We should get together sometime outside of class.” Yeah, that would be cool! When are you free? “I don’t have much this weekend. Want to grab coffee or something?” I’m down for that. Let’s check out that new cafe on the corner. “Hey, we should get lunch sometime this week. Are you free Friday?” Sorry, I’m really busy on Friday. “What about the weekend, or sometime next week?” Sure, I’ve got some free time on Monday and Tuesday. “Do you want to get lunch one of these weekends?” I’ll be out of town this weekend. “Okay, what about sometime next week?” I’m pretty busy for the rest of the semester. “Okay, no problem.” Tell him exactly what you want to do. Don’t: Ask if he’s free without mentioning a specific plan or event. “Hey, are you free tomorrow at 9 pm?” Um, not really, I have work the next morning so I should probably get to bed early. Do: Lead the conversation with your plan. “There’s this awesome light show tomorrow at 9 pm. Want to go with me?” That sounds great! I love those things.