Unless you've both decided to have a formal session of getting to know each other by asking any questions that have been on your mind, keep things low-key.
Let the questions follow each other naturally as the conversation unfolds.
Ask one of the lighter questions and follow that path until you get to a point where you can ask more serious ones.
Don't sit down at a restaurant on a first date, order your drinks, and immediately launch into rapid-fire questioning or there may not be a second date (what a total disappointment if you liked their answers! Once you both know you're interested in learning a lot more about one another, consider the more structured "Twenty Questions" type of conversation, whether you're just talking or including it as part of a game.
The reason is because you’ll come off like every other horn dog guy. Asking questions during a phone conversation isn’t something you do randomly. Asking the right questions and in the right order can make a lasting impression and can make sure you get the date.It’s also an essential part of being a great conversationalist. If you’re confident, ask if she or he would like to continue the date someplace else. ) alternate ending to the night rather than simply going your separate ways after drinks or dinner. There’s this cool bar I know around here, want to go grab a drink? Want to get coffee/dessert after this somewhere else? My friend’s actually having a party a few blocks away, do you wanna stop by? This phase is tricky, and should only be reserved if you’re really feeling strong vibes.