Check for interest first
Look for a person who prolongs conversations with you, remembers what you said last time, finds reasons to be near you, and asks questions about your life. None of that is proof, but several of those signs together are reason enough. If you truly cannot tell, asking is the only way to find out, and an honest question put politely offends almost no one.
Make it specific and clear
Three things make an invitation work. It names a plan, it names a time, and it uses words that make it plainly a date. "We should hang out sometime" fails on all three counts.
- In person, say, "I have really enjoyed talking with you. I would like to take you out for a drink on Thursday, if you are up for it."
- By message, say, "I would love to take you to that ramen place you mentioned. I am free Saturday evening, and no pressure either way."
- To a friend, say, "I have started to think of you as more than a friend, and I would like to take you on a proper date. If you do not feel the same, I will be fine, and nothing changes."
Keep the first plan short and inexpensive, such as coffee, a drink or a walk. Ask out of earshot of a crowd, so the person can answer freely.
Where to be careful
Think twice before asking someone who is at work and cannot walk away, such as a server, a bartender or a trainer. If you do, leave your number with a light word and let them decide, instead of asking for theirs. With a coworker, check your employer's policy, ask once, and never ask anyone you supervise or who supervises you.
Taking the answer
A yes needs only a confirmed time and place. A counteroffer, such as "I cannot do Thursday, but I am free Sunday," is a yes. "I am really busy right now" with no alternative is a no delivered kindly. Reply with, "No problem at all. I am glad I asked," and carry on as before. Do not ask why, do not ask again next month, and do not go cold on the person afterward. How you take a no is the truest test of your manners.
Tip Decide your exact sentence before you open your mouth. Most of the awkwardness in asking comes from the rambling preamble, and a single clear sentence needs none.
