KILLER CONVERSATION STARTERS SO YOU CAN START A

CONVERSATION WITH ANYONE, ANYTIME

How can you have dazzling conversations with everyone you meet? I have a few tips and
tricks to using easy conversation starters that lead to amazing and memorable conversations.
A good conversation starter topic can make a normal
conversation great. I have broken down this post into
different types of conversational situations you
might find yourself in. These conversation starters
can help spark interesting, deep and memorable
conversation with anyone.

CONVERSATION STARTERS FOR ANY SITUATION:

Let’s start with some killer conversation openers. These are great for simply opening a
conversation with someone new or someone you haven’t seen in a while. And they’re far
more interesting than the standard “Where are you from?” and “what do you do?” those are
so boring. Try these instead.

▪ Tell me about you

This is a great one because it invites the other person to tell you something that they want
to share. If they want to tell you about their job, they can. If they want to tell you about
their kids, they can. And it’s a great way to know what’s at the top of someone’s mind.
▪ Working on anything exciting lately?
This is my alternative to “what do you do?” Asking if someone is working on anything
exciting helps the other person talk about something good in their life, as opposed to just
giving you a boring update.
▪ What’s your story?
This is an interesting conversation starter because it invites someone to tell you a story
about them, and you never know what exciting thing they might tell you.
KEEP THE CONVERSATION GOING:
Okay, those are my twelve killer openers. How about getting more personal? My next set of
conversation starters are to help you continue the conversation.
▪ What are you doing this weekend?
Ever had that awkward lull in a conversation? This
conversation starter is always welcome. And, if it is
a Monday or Tuesday, you can modify it to ask “Did
you do anything fun this past weekend?” Sometimes,
I also try “What’s your favorite thing to do on the
weekends?”

▪ What are your favorite restaurants around here?

I almost always ask for personal recommendations. They make great conversation
starters. Why? I always get great tips! And if someone doesn’t have an answer because
they are new to a city, you can talk about where they came from. Win-win!
▪ Keeping up with __sport / tv show / news__ recently?
If you are up to date on news or sports, you could also ask your partner if they keep up
as well. If so, great, you have a lot in common. If not, you can tell them about it!

TAKE YOUR CONVERSATION TO A DEEPER LEVEL:

Let’s say you have been speaking to someone for a while, or it is a friend you have seen many
times before and you need MORE to talk about. These are my deep conversation starters.

▪ If you had to pick any character in a book,

movie, or TV show who is most similar to you,
who would you choose? Why?
This is great if someone has just talked about an actor
or book or movie. It tells you a lot about a person to
hear which character they feel most like.
▪ When you were growing up, what was your dream job? Is any part of that still
true?
I love asking this one anytime someone has just mentioned something about their
childhood or growing up. It also helps you talk about whether their current job is similar
to their original dream.
CONVERSATION STARTERS FOR WORK APPROPRIATE TOPICS:
The most successful professionals know how to both be productive at work and be likeable.
How can you do this? You have to use the right conversation starters to open genuine,
authentic conversations in the office. I love all of the conversation starters I have already
mentioned for trying with your office colleagues, but here are a few more.

▪ Is there a charitable cause you support?

Sometimes at work all you talk about is… well… work. This
question is great to learn what someone is passionate about
outside of work. Make sure you have your favorite charity
picked out before you ask so you have a great answer too!
▪ I’m a bit nervous about the _____. Have you ever
done it before?
Sharing personal information to others can increase how
likeable you are perceived to be, and can help form new social bonds. You can use this
trick to start a conversation at work with a colleague, and get some good advice on
whatever challenge you’re currently facing–whether it’s a new piece of software or a
difficult client.
▪ What has been the best thing about working here?
This is especially helpful if you are starting a new job. You can also use this one if
someone new has joined the team and you want to share your favorite thing with them.

CONVERSATION STARTERS FOR A FIRST DATE:

So you’ve ordered your drink and found a nice table. You know how to flirt, but do you know
what to talk about on a first date? The best conversation starters for dating are ones that can
give both of you an insight into the other’s personality and life.

▪ What job did you want to do when you were a kid?

Maybe they wanted to be an astronaut, or a vet. You can ask follow up questions too. Are
they still interested in space studies? What changed when they grew up. Do they love the
job they are in now? This type of conversation starter can open up topics such as future
goals and professional development too.
▪ If you had to pick one–skydiving, bungee jumping, or scuba diving–which would
you do?
 This first date question is great to figure out if your date is an adventurer. It might turn
out that they have done one or more of these things already. Or, they might be terrified
of the idea of any of them. And if you are adventurous, good news: adventurous people
are usually considered more attractive. Either way, you’re bound to get a great answer
and an insight into the way they approach risk.
▪ What’s the most important thing I should know about you?
On a first date, you are trying to really get to know each other. Basically, you are trying
to suss out if someone would be a great fit for you (and you for them). This question is a
great way to get to the heart of the matter.
FUNNY CONVERSATION STARTERS:
Funny conversation starters can be used in (almost) all of the situations above and they serve
only one purpose: to make people laugh.
Laughter is important for bringing people together, so you’re sure to be the life of the party
with one of these funny conversation starters.

▪ What was your worst fashion disaster?

Everyone has a few outfits from their past that seemed like a good idea at the time. This
conversation starter will help you get to know what the people in your life were like
before you met them. It will probably come
with a few great stories about their days as an
early 2000s emo or 1960s mod. What makes
this funny conversation starter especially useful
is it can cross the age divide, bringing older
members of the party into center stage with
fashion faux pas from the past.
▪ What’s the most embarrassing thing you did at school / when you were a kid?
This conversation starter works best in groups, when people will have time to think of
their own story while laughing at the others sharing theirs. Reminiscing about the past
can make people feel calmer (so it may be worth cracking open this conversation starter
on a tough day at the office).
▪ If you had a reality TV show about your life, what would your theme song be?
It’s a good way of talking about music without asking people what bands they like (which
can be a bit stilted and boring), and it short-circuits any indier-than-thou posturing in the
name of fun. Bring it to life in the style of a ‘90s sitcom by probing people on the cheesy
clips that might accompany their montage bonus points if you get your friends to suggest
your theme tune).
BIRTHDAY PARTY CONVERSATION STARTERS:

If you have a birthday or are celebrating someone else’s birthday, I always ask these to get
the conversation going:

▪ To the birthday person:

“What was the highlight of your last year?” Or, “What do you want to achieve for next
year?”

▪ To fellow celebrators:
“How do you usually celebrate your birthday?” Or, “What was the best birthday you ever
had?”

▪ To everyone else:
“What was the best (or worst) birthday gift you ever received?” This is a great one to do
around a dinner table. The answers are always hilarious.