Where would you like to go?
Before asking him, think about where you want to go. As part of this, consider how much it will cost, how far away it is, how long the activity will take and whether you have already done something similar before. Do you want the date to be just the two of you or would also like friends to come along?
Choose an activity that both of you will enjoy. While making a compromise now and then to do something he likes a lot that you don't much care for is part of the relationship, if this is the first time for asking him on a date, choose something you will feel comfortable about too.
Ways to ask your boyfriend on a date
Consider the method you'll feel most comfortable with. This will depend on your relationship and how you usually contact each other too. You can text him, call him, email him, talk to him on IM (instant messenger), write him a nice letter, or speak face to face. You might also like to contact him one way, then follow up with another way, just to confirm his affirmation to going on the date, and the time, etc.
If you feel really worried about how he will respond, try face to face. It's a lot harder to say no or push aside someone's kind request when you're face to face. He'll see immediately how much effort this requires of you and be more willing to meet you all the way if you are together when you ask. Have courage––he cares about you after all!
Asking him
Just relax. He is your boyfriend, after all. While he might say no, he is more likely to say yes, or to suggest you make another suggestion if he does say no. He isn't going to bite you or laugh at you; if he does, he's not boyfriend material.
Ask him what he is doing on the date you'd like to arrange the activity together. For example: "Are you doing anything this weekend? I have an idea for something we could do together." "Any chance you're free this coming Thursday night? There's something I'd like to suggest we do together." "Would you be free next week? I'd like to go somewhere together for a few days of the vacation if you are."
If he says he's free, go ahead and ask him on the date. Tell him what you'd like to do together, why you think it'd be fun and any other relevant details to help him reach his decision.
If he says yes, that's a great idea, well done! Start planning the activity together.
What if he says no?
If he says he is really busy, don't push it. He actually means it and being pestered about it will end up irritating him and could sour things for you both. Just say something like: "Okay, maybe another time then", or "No problems. It'll keep until you're free." He'll appreciate the lack of pressure and the willingness to change your plans for him. Leave off asking him again for at least a week. That way, you won't seem pushy or desperate.
If he says no because he doesn't like what you've suggested, be ready with an alternative. For example, if he says he has already seen a movie or doesn't like the genre you've suggested, have one or two different ones to offer instead. Or, switch from movies to skating/a sports game/dinner out, etc. Be ready with flexible options. Other possibilities include going to the park, the beach, out of town, etc. Another option is to ask him what he'd rather do. However, it's a good idea to offer your ideas first, to show you've really thought about this.
If he says he needs to think about your suggestion, take it at face value. He does need to think about it. This does not mean he is not interested in you; it means he needs to think about the activity. Feel free to say something like: "Sure, no worries. If you do want to, maybe you can let me know by tomorrow/Friday/the weekend, so that I can book tickets/reserve the seats/etc.".
Don't force him. That's a good way of him dumping you. There are plenty of other times to ask again. If he keeps declining your suggestions, it's a good idea to ask him what he'd rather do. If you feel you can't ever make suggestions, you might need to rethink the viability of the relationship, as all relationships are about give and take.
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