It's one of the hardest things to do when dating: ask someone out. And in this post-liberated world of ours, both men and women do the asking. Fear of rejection is frequently cited as the most common reason why people are afraid to ask out someone they like. We hate to burst your bubble, but it happens. If you do any amount of asking out, you will eventually get rejected. It's not you: it's just the law of numbers.
So we're not going to tell you how to get the other person to accept; that's their choice. But we will tell you how to ask so that you reduce the chances of rejection.
Don't Be Vague. Propose an Activity
The wrong way to ask: "Want to go out?"
The right way to ask: "Interested in going to the chocolate festival this weekend?"
See the difference? The first one is vague. The second one is a definite set of activities. Nobody likes to be asked to make a decision about a fuzzy statement. Have you ever had someone ask, "Can you do me a favor?" while wondering what this "favor" may entail? It could be you giving your opinion on someone's hairstyle. Or it could be you loaning them, $10,000.
Be Brief and Clear About What You Are Asking
"Um, hey, you know. Supposed to snow this weekend. I was thinking about going skiing on Saturday."
See anything wrong here? It's not a question. It's not even a request.
A question would be you saying, "Would you like to go skiing?' A request would be: "I want you to go skiing with me. Let me know if you're interested."
Make your "asking" either a clear and brief question or a clear and brief statement. Don't leave the other person hanging.
Group Activities Are Often Easier
It eases the pressure on everyone when you ask if the other person would like to join you for a group activity. A group activity is something like a bunch of men and women river-rafting for a couple of hours.
The gender mix is balanced: not too many men, not too many women. Guys, you never want to invite a girl to a guys-only event. It's not fair to her—or to your buddies. Girls, same thing.
Be aware that inviting that special someone to a group composed only of couples changes the dynamic between you and that someone. It sends signals that you are interested in that someone in a romantic way. Not necessarily a bad thing, but something to be aware of.