2. Ask him out right after work: “Do you want to grab dinner?”
“It’s normal to go grab food or drinks with a colleague after work. I wouldn’t say no unless I have other plans,” a guy in his 30s explained. The best way to ask your coworker out is to make it seem like an after-work get-together. If he’s staying late at work, you should do the same and approach him as he’s finishing things up. This will make your approach seem more natural.