At least not like this
Being vague by saying “I’m free whenever” and “we can do whatever” gives off the vibe that you’re not committed to making concrete plans. The date is morelikely to happen if you just pick a day, time, and activity.
It’s one thing to be bold, it’s another to come off as too intense. Don’t bombard them with too many questions or quadruple text before actually asking them out. Read the room and keep it simple by laying out a game plan.
No one wants to be rejected, which is why asking someone out can induce anxiety. Just chill though! At the end of the day, they’re either going to say yes or no. If it’s the latter, you're still going to be just fine.
Bringing more people into the mix may give them the idea that you’re not actually interested in getting to know *them* (or you're too scared to hang alone). Suggest a one-on-one hang out first.
There are plenty of ways to ask someone out that don’t involve a corny pickup line. They would much rather you be yourself when asking them out than trying to come off as some witty pun wizard.
If you've been going back and forth with conversation on a dating app for a while now, don’t assume they’ll be the ones to ask you out first. Forget the outdated rules by taking the initiative, giving them your number, and setting up the date yourself.
Let’s say you already had a date and you’re *really* down for a second one. Don’t wait around too long without asking them out, otherwise, they may think you’ve moved on or ghosted them. If you’re into them, let them know it and show it.
Look, they might not be into you. If so, leave your ego at the door and learn to take "no" for an answer. Don't get wrapped up in romanticizing persistence when it's really coercion.
Creating unnecessary pressure or doing a big public gesture might make them feel like they can't say no. Think about how you might feel in their shoes if they weren't interested and be sensitive to that that possibility.
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