#6. Have a Basic Script Ready. There’s no need to have every single line you’re going to say polished and rehearsed, of course, but it’s a good idea to have a basic idea of what you’ll talk about ahead of time. Make a mental note of how you’re going to open, what you’ll say in the interim and how you are going to phrase asking her out.
Be straightforward and polite, and make your intentions clear: there’s no point darting around the fact that you’re looking for a date. Use straightforward language like “would you like to have dinner with me this weekend?” or “Are you free for a drink after work this week?” rather than “it’d be cool if we could hang out some time” — that way, there’s less room for confusion.
#7. Have a Follow-up Idea About Your Plan. Let’s say she says “yes” when you ask her out on a date. Congratulations! That’s the ideal result. However, you’re going to need to think about what to say as a follow up — you’re going to look silly if she says “what kind of date?” and you’ve given this no consideration.
Dinner or drinks at a nice bar are a pretty safe fallback option, but avoid saying “I don’t know, what do you want to do?” — it makes you look flaky and indecisive, and puts the work on her to think of an idea even though you’re the one who has requested the date. Propose an activity and set a time, and then gracefully exit, and let the rest of your conversation take place on the date itself.