Engaging in a conversation with someone we’re interested in dating isn’t that hard. But when it comes time to actually ask someone out, that’s another story. If you don’t know how to ask someone out the right way, it could make all the difference in whether you’ll land the date or not.
To help you out, we put a list of four situations you may find yourself in, and what to say and what not to say when it comes time to ask the other person out.
Situation 1: You matched with a new interest on a dating site or app and have been chatting NON-STOP for hours, a day, or a few days. You feel there’s a connection and seem to have hit it off via text and now you want to finally meet in person.
Say this: “You seem great; I’d love to meet up some time. Are you around next week?”
Dating coach and founder of Sexy Confidence, Adam LoDolce, suggests going about it this way because it’s casual and doesn’t put too much pressure on either of you. This is a safe way to go whether you’re talking on the phone or still communicating via text.
Not this: “We should hang out.”
It’s not so much the words but the vagueness. Hang out when? What do you mean by hang? There’s nothing worse than engaging in what seems like endless text conversations with someone who has no intention of asking or agreeing to go on a date with you.
Situation 2: You’re out with your friends at a lively bar having a few drinks when before you know it; you’re engaged in a deep convo with a stunner who caught your eye. You feel like you’ve discussed everything from where you work to your favorite ice cream flavors. Now the night has come to an end but you want to see this person again… and soon!
Say this: “I’d love to grab your number, maybe we can get a drink or a cup of coffee sometime.”
You definitely don’t want to leave without being able to communicate afterwards, so LoDolce advises to exchange digits first, and then hint at a date.
Not this: “What’s your Instagram/Facebook?”
This implies that you may not have any intention of asking the other person out or going out with him or her until AFTER you stalk the life out of them. As a result, it may put people off.
Situation 3: You’re on your bi-weekly stop at Trader Joes and it seems like you and the looker in produce are on the same schedule because you keep seeing each other there. The other person noticed these repeated meetings too and you start to briefly engage in a discussion in the checkout line.
Say this: “I know this is a little forward, but I’d love to grab your number and see you again.”
If you’re wondering if it’s okay to ask someone out after meeting this way, LoDolce says, absolutely. “This is OK and handled basically the same way [as meeting at a bar], but with a little preempting.”
Not this: “Let’s go on a date.”
Not only is this a little too forward in any situation, it’s ESPECIALLY forward—and a little creepy—in a situation like this.
Situation 4: There’s this co-worker, or friend of a friend, or just somebody that you’ve known for a long time. You’re friendly with each other and communicate often. You feel that there’s a possibility you could be more than friends so you decide you’re just going to go for it and ask this person out.
Say this: “I’ve been thinking that we should go grab dinner sometime…”
LoDolce says dinner implies a romantic date rather than a drink/coffee, which could be misconstrued as friendly. You’re already friends; the point is to be something more and make that clear.
Not this: “I can’t stop thinking about you. We should go out and see if this is something more.”
This is also too forward and suggestive, especially since you have no idea if this other person is feeling the same way.
Knowing how to ask someone out is always a little rough, but don’t forget that it’s a natural part of dating and something all people have had to do at some point. Use the words above or put your own spin on them and go for it. After all, what’s the best that could happen?