How to Break the Ice and Cut the Small Talk on a First Date

Be honest– small talk is painfully boring and uncomfortable…and you’re guilty of it (as we all are).

However, that’s amplified when the situation in question is a first date, where you’re trying desperately to not only get the other person to see who you really are, but also get to know them intimately.couple-enjoying-successful-date-night

There’s a lot of cheesy and annoyingly general advice out there on how to break the ice in conversation (“just be yourself!” “make them laugh!”) but, in practice, most of it is usually pretty difficult to pull off intentionally.

Fortunately, there are some more practical steps you can take to break the ice and get into some good, deep conversation, the kind that defines a great first date.

Just be funny. Funny always goes over well, so try to think of something funny to break the ice rather than being weird or using pickup lines.

– Charli XCX

Here’s how to break the ice and cut the small talk on a first date.

1. Never, ever ever, talk about the weather

Some of the tips below are great conversation starters while others are tips for creating great conversation in a general sense.

This is neither of those; it’s a warning.

Never ever ever, ever ever ever, ever talk about the weather.

Okay, I’m not talking strictly the weather but any super standard, I’m-stuck-with-a-stranger-at-a-crosswalk type small talk. Anything like discussing the weather, or the day of the week, or month of the year, or how fast the year has flown by, or anything else similar to that, isn’t just bad, it can literally be catastrophic for the conversation.

As soon as you mention the weather, or something similar, the other person will often check out completely and write you, or at the very least the conversation, off as boring and dull. Coming back from that will be far more difficult than if you had said any one of a million other things.

So just…don’t do it.

2. Write down some conversation starters and keep them on hand

people-having-a-conversation
Photo Credit: Bryan Apen on Unsplash

So, don’t talk about the weather…got it.

The next obvious question is, what do I talk about then?

It’s not much use to tell you what not to talk about (or how to make absolutely certain you stay ice cold) without giving you tips to break the ice.


These days, it’s so common for people check their phone that it’s easy to take a few minutes to write down some good conversation starters beforehand, text them to yourself or keep them in your notepad, and quickly pop out your phone under the table or slip it out of your pocket and check them if you’re stumped mid-conversation.

This is probably the best tip there is because no matter what, you know that if you have those few notes you can consult in a moment of despair, you can get your conversation back on track (or keep it that way).

Examples of conversation starters include:

  • Asking them what they do for a living, how they like it, how they got into it, or how they feel about what they do
  • Asking them about their passion(s)
  • Asking them about their major goals or dreams, or any major regrets
  • Mentioning a cool article you read or video you watched (could be a new scientific discovery, some funny prank, interesting fact, or anything else that interests you– especially useful for expressing who you are while also testing their interests)

3. Ask a deep question about a shallow topic

It’s easy to start shallow conversation — mentioning the latest bit of relevant news or anything pop-culture will get you there. However, that’s obviously not far beyond that icy stage you’re trying to get out from.

Instead, find something your date is interested in, and simply ask a deep question relating to that shallow topic.

For example, the flow could go like this:

Shallow conversation starter: Did you see they casted the new Batgirl?

Deep question: Did you see what happened to her on Twitter? What do you think about bullying on social media?

This immediately jumps the conversation into something deep and meaningful with little effort. And the cool thing is you can use this tip with virtually any topic imaginable.

4. Ask open-ended questions relating to the other person

If the above still hasn’t helped you, another tip you can use is to ask open-ended questions.

Don’t ask the other person how their week was, or if they like their job, as those can elicit a very simple yes/no answer or an equivalent.

Instead, ask them this version of those same questions:

  • What was the best/worst part of your week?
  • What do you like/hate most about your job?

These are open-ended questions that spark conversation and get your date to share stories and open up about how they feel about certain things in their life.

5. Assume the other person wants to have a deep conversation with you

If all of that still doesn’t work, there might be one very specific problem: you’re treating the other person like they just want to hang out and chill.

If you really think about it, as much as you want to have a deep conversation, you might be treating the other person and speaking to them in a way that suggests you’re just trying to hang out and have a very shallow, fun time in an effort to impress them (a little too hard).

But if your goal is to really get to know the person and have a great, meaningful interaction, then your best bet is to treat them like they are too — even if they aren’t. The truth is, if you are and they aren’t, they’re probably not a fit for you anyway, and it’s best you find that out sooner than later.

So, instead of asking them shallow questions about what they like or hesitating to ask them a deep question that’s on your mind, just jump in and go for it.

Most other people are like you, I promise you, in that they crave real, deep, meaningful connections and want to get steeped in a great moment with someone.

Yes, especially on a first date.


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