Ok so I have this friend and for reasons I won’t get into we’ll barely ever be in the same place at the same time anymore unless we plan it, and I’ve never really had to initiate planning things like that so I’m not exactly sure how I’m supposed to. Thanks in advance :)
Usually I will take an interest I know we have in common (movies, sports, museums) and text something like, "Hey, I really want to go see x movie, do you want to come?". If they say yes, I say, "Great, is x day and x time good for you?". If they are non-committal, I take it as a no. And if they say no, I say, "OK, no worries :)" and go back to the normal way we interact.
For me, finding something that someone else is required to be there is handy I think. Like "I have two tickets for bowling on Friday, but my sister/brother/bf/gf couldn't make it, and the place doesn't offer refunds. Do you want to come?" You can change bowling to cinema, amusement park, concert, whatever suits you. And then when you guys have been there, you can casually say "we should do this again sometime, this was fun" and if their reaction seems positive you can text them a few days later or whenever suits you asking them to do something else with you
Since I’m usually a pretty busy person with a lot of busy friends I’m very direct when I ask people to hang out. I like to have my schedule on hand and have two or three activities in mind just in case they prefer one over the other. Then I just go straight for it and say something like “I would love to hang out more, are you free anytime this week?” If they are, cool! Make sure you are available at the same time and offer up your ideas for things to do and, boom, scheduled. If they aren’t available ask them if they have another week for time they would like to hang out. If they have another time that works, then use that. If they decline or don’t commit to setting a date (ex: “I’ve been busy lately and don’t know when I’ll be free”), simply thank them for trying and make it clear that they are okay to reach out to you if they ever have time to hang out.
I’ve found it’s best to have an activity in mind. Like asking “do you want to get lunch?” Or “do you want to see a movie?” Is better than just asking someone to hang out. And it’s helpful to offer a day and time. Like “Want to come over and watch a movie Friday?”