9 Ways to Recover From a Failed Conversation Starter

Despondent after you have failed to impress her (or him)?

By Fred S.
9 Ways to Recover From a Failed Conversation Starter

Conversation Starter that Did Not Go Well

We’ve all been there. A certain starting line doesn’t go as well as it did in our heads. It’s normal for that to happen as there are plenty of reasons why things can go wrong with conversation starters. Who knows? We’ve all been there. A certain starting line doesn’t go as well as it did in our heads. It’s normal for that to happen as there are plenty of reasons why things can go wrong with conversation starters.

Who knows? Maybe the other person has been having a terrible day.

Maybe their dog died.

Maybe someone bumped into their car.

Maybe they got into a fight with their boss.

It could be anything! All of this affects one’s mood and greatly reduces your chances of getting along with them with a fun little convo-starter. The most we can do in such situations is either move on or try secondary conversation starters that are safer bets.

In this article, we’ll go over nine proven ways to start a conversation healthily and positively, even after you’ve failed your first attempt. Let’s get into it!  

9 Ways to Recover From a Failed Conversation Starter

1. Offer a helping hand

No matter how bad your first conversation starter went, or how bad their day has been, a helping hand always ‘helps.’

It’s a great way to get somebody’s attention, especially when you see them struggling to figure something out. If you think they’re overwhelmed, try offering to hold something for them. Things just as simple as holding their phone and Starbucks cup can make people appreciate your presence at that moment. It already wins you a lot of their trust. From there, you should be off to a good start!

2. Give a compliment out of the blue

This one can be used in conjunction with the first one, or independently as well. After you’re done helping them, allow them to thank you, and break the ice with a compliment! These days, compliments don’t come very often, so they’re more welcome than ever. You could experiment with it all the time, just compliment what people are wearing, and they’ll give you a free smile in return. It’s a great way to spark a conversation – because who doesn’t like compliments?

3. Ask for a helping hand

Not only do people love getting assisted, but they also enjoy helping. There’s a feeling of bliss in being truly useful for a stranger, and you could use that to your advantage! ‘Helping’ forms natural bonds, even if you’re meeting someone for the first time. It lowers walls and builds mutual trust.

An example of asking for a simple helping hand can be when you’re walking down the fruit aisle and ask a stranger if they think it’s ripe enough. You seem open to learning more, and the other person gets placed in a position of authority. Whatever their reply is, you thank them, and flow the conversation naturally with a question about what they’re shopping for here.

4. Use a self-deprecating line to recover

When a conversation starter fails, there’s usually some awkward tension in the air between the two parties. You could easily clear that out with a self-deprecating line like, “Oh, that was a silly question – I feel so dumb right now, haha.”

All of a sudden, the other person laughs and tries to make you feel better. It clears the air and instantly helps the two of you engage in a positive-toned conversation.

5. Compliment something beside’s the appearance

Compliments are great, but deeper ones are even greater. Instead of resorting to complimenting something like their eyes or their hair, go for something less generic. You could appreciate aspects that speak about their personality, like the book they’re holding, or the message on their top! It’s an elegant way to boost someone’s interest in you if you like them. You could use this for business and social reasons too!

6. Hit em’ with something mind-blowing

Facts, riddles, and trivia are incredibly effective ways to pique peoples’ interest. In an instant, you could recover from a failed conversation starter with something like, “Let’s play a game. Name three countries starting with N!” [Netherlands, Norway, Nigeria]. It immediately gets people thinking, and they forget the awkward or failed first encounter. A few minutes later, circle back to them and see if they found all three countries. They’ll be thinking about it, and you!

7. Get deep

A light philosophical twist never fails to make your personality a bit more intriguing. If you’re sitting in a serene environment where people are enjoying their surroundings, you could say something like, “isn’t this what life’s all about?” after a slight silent pause. It’s dramatic, but lets you know if a person is up for talking to you!

8. Ask a question with no right or wrong answer

Some questions can be casually thrown into a conversation, regardless of how it’s going. It’s nothing to worry about if you’ve failed with your initial conversation starter. Ask something like where they’re from, which is a natural way to encourage people to talk about themselves. Such open-ended questions work great every time because people enjoy sharing details about themselves. Besides, everyone’s answer will be unique, so you’ll never get bored of listening either! Things can become interesting real quick if you both find out commonalities among each other, such as being from the same city!

9. Be pleasant

Positive vibes are attractive, and miserable ones aren’t – that’s just how it is. It’s a universal truth; people are interested more in those who exude happiness and seem content with themselves. The best conversation starters don’t just have to be one-liners, but they can also be manifested and practiced in one’s attitude.

Try to start your conversations with something pleasant that makes people appreciate the moment more than they were. Point out how you think the night feels beautiful! It helps the two of you ease into a conversation because even a sudden “hey!” out of nowhere can be quite shocking.

How to Impress Again After a Failure

The first step is to use one of the conversation starters we’ve listed and described above. But, that might not be enough. To set you up for a successful recovery after failing, here are some helpful communication tips to get you going;

1. Listen more

The key to any piece of valuable conversation is the strength of your listening skills. Give your mouth a rest every once in a while, and say no to interrupting others, no matter what. Activate your ears! Give people your unshared attention and wait for them to ask about you themselves. If you hear words like ‘What do you think?’, you can be sure that a connection has been successfully established.

2. Take a break from asking more questions

Back-to-back questions can quickly start feeling like an interrogation for the other party. It also sends a message that you don’t have much to contribute to the convo, which isn’t so interesting for others. Remember to mix things up by adding statements that communicate your ideas more often. Your ideas craft your personality, and questions inquire that of others – so make sure you strike a healthy balance.

3. Speak clearer and slower

Communication is a two-person job, always. You can’t just work on your listening skills and neglect your delivery. It’s not always about what you say, but how you say it! You could be successful in maintaining a healthy conversation just with great delivery skills.  

Speak clear and slow. When we get excited about sharing an idea, we tend to talk faster and mumble more. That stuff isn’t too engaging for the listening party. Make it as easy as possible for them to comprehend what you’re saying by speaking calmly and clearly.  

Learning to Move On

If you’ve messed things up in the beginning, it’s important to understand that it’s not just you who’s dealing with the awkwardness. The other person is probably just as uncomfortable as you, so have empathy. Often, the natural impulse is to say more things until it works out, but that’s not the best idea.

If you continue to get negative body language signs that tell you the other person isn’t enjoying your company, it’s fine to accept the L. That’s just how it is sometimes.

It’s sometimes better to move on than making things worse. You might be ruining someone else’s evening by lingering too long, and that’s not cool. Instead, wait until another opportunity arises (with the same or a different person) and start with one of the safer conversation starters we’ve described. Follow that up with the communication tips we’ve shared, and things should go just fine.  

Related Article: The 100 Best Conversation Starters For Girls
The 100 Best Conversation Starters For Girls

Girls, are you struggling to find the right words? Here are 100 conversation starters that will help you break the ice and get the words flowing.


The key take away is that to seem interesting, you’ve got to be interested in the first place. It’s appealing to talk to someone interested in hearing about us, so it’s safer to start things that way. The conversation starters we’ve listed accomplish this effortlessly as they’re you-focused, and not the other way around.

Remember though, just because the conversation has begun successfully, doesn’t mean it’ll stay that way. You’ll have to employ active listening and good delivery skills, which can be learned with practice. All the best!