How to Keep the Conversation Going During a Date

Awkward silence.

We’ve all experienced it at some point or another, though I’m sure we all can agree that silence never feels heavier than during a date with your crush.

We obviously want to get to know each other better, come across as cute, witty, and charming, and ultimately decide whether it’s a relationship worth pursuing in the first place. But how can we keep the conversation going, achieving all of the above, without coming across as forceful, blunt, or generally lacking in social skills?

Find a Starting Point

We all know going on a date is a big deal, so even if they’re better at hiding it than you, it’s pretty safe to assume that your crush is just as nervous as you are.

That being said, if your partner hasn’t already started the conversation, taking initiative and starting it for them goes a long way and helps to make you seem more charming and at ease.

Luckily, when it comes to a keeping a conversation going, starting one is the hardest part – which, alternately, when you’re on a date, becomes the easiest!

Upon first picking him or her up, compliment them on how they look, go over what you have planned for the date, or ask how their day was. Listen to their reply, and look for an opportunity to put in a reply of your own. Keep repeating the process, and before you know it you’ll have already dived head first into a healthy conversation with your crush, that can only deepen with the night!


Avoid Questions with One-Word Answers

Look on pretty much any dating site and you’ll find list after list of questions you can ask your crush – you know, questions like “what’s your favorite color”, and “who’s your favorite actor”.

The problem is, while these questions can be great when used as a guide, they do very little to lengthen a conversation when taken at face value, tending make your night feel more like a bad interview than a date.

Instead of rehearsing the old clichés, dive deeper by asking why they feel the way they do, while trying to be as natural as possible in your delivery. For instance, instead of asking “what’s your dream job?”, you could say “you mentioned you were an accountant. Do you like your job, or would you work somewhere else if you could?”.

Notice the difference?

Instead of a one-word answer, with a long pause afterwards as you try and find another question to ask, your crush is inspired to not only talk about the reasons why they do or don’t like their current job, but the reasons behind their dream job as well – affording you a crucial glimpse into their motivations and passions, as well as showing them that you’re a good listener.

The internet’s “20 Questions to Ask Your Crush” definitely have their place – especially if you and your date decide to play a game where you each take turns asking each other a question – but when it comes to a meaningful (and long!) conversation, their best use is simply as a directional.


Be a Good Listener

Contrary to what you might think, the real art of a good conversationalist lies not in how well you speak, but how well you listen.

Whether intentional or not, over the course of your date, your crush will reveal hundreds of important little tidbits about themselves through the way they speak, their actions, and even what they try to gloss over. Your job is to be paying close enough attention to notice these things, log them into memory, and then introduce them into conversation later.

Using the above method of asking deeper questions, listen carefully to your date’s answer. Maintain eye contact, laugh at their jokes, and show them that they have your full attention. Try not to interject or interrupt them mid-story, but rather note what you were going to say and wait until they are finished to talk.

Their answer will not only give you insight into who they are as a person, but will provide you with the material you need to keep the conversation going!

Being a good listener, however, doesn’t mean that your crush should do all the talking.

On the contrary, as much as you want to get to know your date, your date wants to get to know you too! Don’t be afraid to give long answers, or to get personal. Everyone loves a good story teller, and your crush will appreciate the chance to ask you some questions of their own.

Regardless of situation, the key to keeping a conversation going is to not overthink it. Relax, smile, and be you! Natural conversation can never be planned, while conversation starters are everywhere in our day-to-day life. Don’t be afraid to be the first to speak, and to speak your mind.

Chances are, your date will thank you for it!


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