“I’m bored and feeling juvenile. Want to play Never Have I Ever?” This one is potentially a bit risky because it assumes a certain level of intimacy. But if he bites, you have a built in excuse to reveal things that might otherwise be too forward or flirty. Plus, you... “My resolution this year is to _______. Would you be willing to pester me if I slack off? I’d really appreciate it.” Particularly good for a man who likes to feel helpful, useful, and in... “What was the name of that _______ (restaurant, museum, movie) you mentioned the other day?” The beauty here is that you’re keeping it casual and asking a simple question. But it’s also a sneaky way this could easily turn into a... After a really good interaction: “Thanks for earlier. I can’t remember last time I had such a good time.” This is a big pile of good. You’re complimenting him, reminding him of the fun you had, and confirming that it really was great for... “Hey! No need to respond to this. Just wanted to say I think you’re making me a better person and I appreciate it.” Talk about making a man feel good – how could he not respond to that compliment? At minimum you’ll get a thank you. But more likely it will spur a... 
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