Casually slip it into a conversation, but remember to make it clear that you are asking her out on a date. “I’m glad we’re walking home together. It’s really nice out.” Yeah, and the leaves are so pretty at this time of year. “Hey Jennifer, can I ask you something?” Sure, what’s up? “Would you like to go on a date with me?” I never thought you’d ask! What time? “Hey Jennifer, can I ask you something?” Sure, what’s up?” “Would you like to go on a date with me?” Um, sorry. I’m not really interested in doing that. “That’s okay! Don’t worry about it, I understand.” What are your plans for tonight? “I was just going to ask you that! You want to go on a date to that new Chinese restaurant?” Sure, that place has really good reviews! What time do you want to go? “I can pick you up at 6:30.” Wait. Is this an actual date, or are we just hanging out? “I was thinking an actual date. Is that okay with you?” Yes, absolutely! Just checking. See you at 6:30! Jokingly suggest to her what it would be like to date you, or plan an “ideal date” together. “What are your plans for tonight?” Pretty boring—just dinner, homework, and bed. “Well if you want to go on a date with me, we can do something more interesting.” “So I have the best idea for a date. I’ll bet you can’t come up with anything better.” Oh, yeah? What’s that? “Early morning hike, afternoon coffee, then pizza for dinner. Okay, your turn.” Everything sounds good except for the pizza, I’m not a huge fan. I prefer sushi. “Okay, you win. Actually, I’d really like to do that. What do you think?”