Break the ice with these tried-and-true conversation starters

Starting a conversation with a stranger can be one of the most daunting, challenging situations you face, and that’s only truer when you are in a purely social setting. Whereas starting up a conversation with a new client or colleague can be easy in a professional setting – as can chatting with a new member of a class you take, a person you encounter at a campground or on a hiking trail, or someone you run across at the gym – when there is no specific common ground between you and this other person, it’s all on you to come up with a great conversation starter.

Harder still is that situation when you want to break the ice and chat with someone to whom you feel attracted. Fortunately, that’s the scenario we’re imagining today. For our purposes, we’ll assume you are on the lookout for conversation starters with a girl you find interesting and attractive.

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The most important thing to remember is that when starting a conversation with someone in whom you are interested, you need to be genuine and respectful. It’s all well and good to try funny conversation starters or to be a bit flirtatious, but it’s more important that you are true to yourself, kind, and courteous. That way, even if your conversation starter doesn’t go as well as you’d planned, you’ll be able to regroup and keep going because you are being yourself.

Also, remember that while we may be looking through the lens of questions to ask girls, and in most cases assuming it’s a man doing the asking, don’t think for a second these aren’t also interesting conversation starters for a girl to ask a guy, a guy to ask a guy, a girl to a girl, or leave gender out altogether. People are people, after all, so conversation starters with a girl can be better thought of as, well, just conversation starters.

Here are five different conversation starter ideas that just might get that lady’s attention and earn her genuine interest.

“What’s the weirdest thing you have eaten in the last year?”

Funny conversation starters can be quite effective when they land properly, and food is a topic most people can talk about at great length. By asking about weird food, you open the chat up to the potential for humor, and by adding a timeframe to your question, you’ll prompt the other person to do some real thinking, which will prime her mind for a real conversation.

“Hey, I don’t really know anyone here – mind if I talk to you for a bit?”

Now, for the record, you can’t use this exact opener if you’re with a group, but you can of course modify it and simply ask to talk to the person. That is, after all, what you want, right? If she responds in the affirmative, you can get pretty far into a conversation with basics like introductions, asking what brings the person to the place you’re meeting, asking about their day, and the like. You don’t have to be clever to get into a conversation, you just have to be friendly. (And for the record, heed her words and/or her body language and leave her well alone if that’s clearly the girl’s preference.)

“Do you prefer text, calls, Zoom, or in-person conversations?”

This is a safe topic that everyone can have an opinion about and that is unlikely to be controversial. If you both agree on a mode of communication, that’s a connection; if you disagree, that’s a chance to explain why. Plus, there is the added potential for a few clever and flirty follow-ups, assuming you can read her reactions to you and they are positive.

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If she says calls or texts, you can say: “Well, then I’ll need your number.” If she says in-person, you can say: “Well, this works out then, doesn’t it?” And if she says FaceTime or Zoom or such, you can say something along the lines of: “You are pretty easy to look at, so that makes sense!”

“What would be your dream job?”

This can be a great conversation amplifier, if you will. While it might be awkward to walk up to a girl at a dinner party or bar and say: “Hey, what’s your dream job?” it’s easy to lead with a topic about which we all have something to say: work. So you could say: “Man, I had the worst day at work. How was yours?” And whether the answer is good or bad, you can slide right into a great chat with the next thing you ask being about her dream job.

“What’s the best thing that happened to you today?”

This question immediately puts things in a positive place. It shows you are an upbeat and optimistic person, which we all want in others, and it invites her to reflect on her day with some happiness and gratitude. The positivity in thinking about a good thing from that day will likely radiate into her initial assessment of you, helping you create that all-important good first impression.

And of course you are setting yourself up to answer the question back when she asks it of you, as any good conversationalist should, with: “The best thing that happened to me today? Meeting you.” Even better? She may say that herself.

OK, so you got the conversation started, now what?

The secret to being a great conversationalist is not having lots of interesting things to say, but knowing how to ask interesting questions. And once you have asked great questions, it’s also essential you engage in active listening, a skill that can be practiced and honed. As for how to ask the best questions, just think about some of those that you wish someone would ask you.

And if the question of cute date ideas comes up as a result of your great conversation, well, that’s a good question to have, isn’t it? And it’s something you don’t necessarily have to figure out on your own – now that you’ve moved beyond the ice breaking of it all thanks to that great conversation starter, you can plan your next steps together.


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