Yes, we know it’s your comfort zone. But it’s not the best first-date location since you’re likely find yourself stuck between playing hostess and getting to know him better. Best to leave the hospitality to professionals, whether it’s at a restaurant or a pub or a movie or a cafe.
You want to relax, hang out with him, see how the evening goes – and so does he. If you’re not having fun, you can always bail out. But if it’s going great, you don’t want to have to leave in the middle of things. And you don’t want him to think you’re putting him on a deadline!
If you ask him, and he’s busy, then just say “Cool, maybe another time, then” – no matter how disappointed you are. Give it a few days before you bring it up again, else you’re going to come across as super-pushy.
Now that IS super-pushy. Offer to meet him at a neutral location. Go to his place only if he proposes it as the venue.
We’ve advised you to not be over-eager, yes, but don’t sound totally indifferent either! He should be able to understand that you’re actively interested in his company. In your effort to be all casual, don’t end up saying something like “Oh, I thought we could get a drink since I don’t have anything else to do that day.” No one wants to feel like he’s your backup plan.
Trust us, you’re going to drive yourself nuts while you wait for your message to be delivered, and then answered! Just pick up the phone and ask him yourself. And if you think you can’t get up the nerve, send a text or an email. Be confident. He will appreciate that way more than the weirdness of being asked out by someone else on behalf of you!
Nothing says “I’m not all that interested” louder than a cancellation. If you work long hours, or have some kind of office crisis happening, make sure you ask him out on a holiday. Calling him at 7 p.m. and telling him you’re not going to show up at 8 p.m. will not make him want to be eager to meet you the next time you ask.
Don’t bring up bad dates as a build-up to this all-important conversation, even if your experiences have been hilarious! You’re going to make him worry that the one you’re asking him out on might just be disastrous.
Please be clear about the fact that you’re asking him out on a date, and not just to grab a bite or catch a movie as a friend. If he goes out with you thinking that this is just a friendly hangout session, and then you make a move on him out of the blue, it could get super-awkward super-quick.
Girl, you’re trying to go out on a date with him. So once he’s said yes, don’t go giving him mixed signals, even if you’re super-nervous and feel like backing out because you’re worried about ruining it. (Also, he’ll probably think you’re crazy.)