50 Conversation Starters to Use With a Guy


Last Updated: April 11, 2024

Sugar Baby

Worried that your conversation isn’t engaging enough to keep him interested? You’ll love this list of conversation starters with a guy from every part of your life! Whether he’s a stranger you’re seeing for the first time, a friend of a friend, or an online match, we’ve got 50 intriguing icebreakers that will spark the kind of back-and-forth you’re looking for!

Conversation starters with a guy you see in public

No matter if you’re out at the bars or making eyes at the newbie at the office, these conversation starters are great for first meetings:

  • Do you think our phones are taking away our ability to strike up a conversation with strangers? 

  • Are you from around here? I’m looking for coffee/bookstore/hiking recommendations

  • Do you happen to have any fun trivia facts that you’d like to share? It’s one of the things I like to ask strangers.

  • What is the best drink this bartender makes in your opinion? I’m looking to try something new.

  • What’s the best way for a gal to ask a guy on a date? 

  • Do you listen to podcasts? I’m looking for recommendations

  • Do you have a soap box rant that you’d like to get the word out about?

  • I know we’ve never met, but I was wondering if you’d be open to receiving a compliment

  • I really like your headphones/computer case/ jacket/etc. Did you get it somewhere around here?

Conversation starters with a guy who shares mutual friends

When you’re interested in a friend of a friend or someone in your existing social circle, you may feel even more pressure to make a good first impression. Don’t worry. These questions are sure to get the ball rolling.

  • So, who in our friend group have you known the longest? How did you meet?

  • Who do you think is the funny one in the group?

  • If you had to characterize our mutual friends as a sitcom, which one would it be and who would the characters be?

  • If our friend group was stranded on a desert island, who do you think would become the leader?

  • What’s a funny memory you have of [mutual friend]?

  • If we all banded together to play a team sport, what sport would you want to play?

  • Who do you think in our group is the worst at keeping a surprise?

  • Who do you think is a better driver?

  • Who in the group has a hidden talent that you know of?

  • Do you think there’s a common characteristic in all of us that makes us friends?

To be sure, you don’t want your entire first conversation to be only about your mutual friends. So, use these conversation starters as a jumping board. From there, you can start to get to know one another more intimately.

Conversation starters with a guy you see often in your routine

Tired of trying to catch his gaze over the crowd at your regular coffee shop? Or, maybe you’re ready to finally make a move on the guy you always see at the gym. Go up to him and introduce yourself with one of these conversation starters.

  • I’ve noticed you here before! Have you tried the new ____ on the menu? I’m thinking of ordering it today.

  • So, what makes this place your go-to? 

  • You know, if you like this place, I have another one to recommend! Maybe we could go together sometime.

  • Since we’re both regulars, which one of the two of us do you think they’re more likely to name a drink/sandwich/etc after

  • Do you do other sports outside of the gym?

  • I see you lift weights here a lot, do you have a protein powder that you would recommend?

Conversation starters with someone you’ve met online


Online dating conversations can get boring so quickly! Prevent online burnout with these interesting conversation topics.

  • What was your go-to breakfast cereal and Saturday morning cartoon as a kid?

  • What are the three things you’re grabbing from your house in the case of an emergency?

  • What is something you thought was overhyped until you tried it for yourself?

  • What is your most useless skill that you are still proud of?

  • If you have pets, how would your pets describe you?

  • What is a conspiracy theory that you know is not true but you kind of wish it were?

  • If you could live in a video game, which one would you choose? 

  • What is a topic that you could give a masterclass on?

  • What is the most frustrating thing about online dating in your opinion?

  • What are your thoughts on astrology?

Conversation starters with a guy on a first date


First-date jitters are a thing of the past when you’ve got a few questions up your sleeve to encourage a good convo!

  • What was your first job? Did you hate it or love it? What did it teach you?

  • Who was the teacher that had the biggest impact on you?

  • What kind of a movie would your life be? An action movie? Comedy? Documentary?

  • If you could have any creative job and be wildly successful at it, what would it be?

  • Who would you first call if you were to win the lottery?

  • What is an opinion you have that makes you feel like a grumpy old man?

  • Do you consider yourself an adventurous eater? Or are you more comfortable with what you know and like?

  • What do you think is a lesson that all young men should learn? How did you learn it?

  • What do you think is going to be the most defining historical moment of your lifetime so far?

Conversation starters with a guy you’ve been seeing for a while

Just because you’ve been seeing each other for a while doesn’t mean that you can’t have fun, engaging conversations! Here are a few ways to relight the spark.

  • What was something that you were nervous about when we first started dating?

  • If I were to write a screenplay, what kind of role do you think I should cast you in?

  • If you were to break down our relationship into a pie chart, what percentages would you put for the following categories: playfulness, physical intimacy, deep conversations, comfortable silence, and eating meals together?

  • Would you rather live with the dinosaurs or live in the future?

  • If I told you to pack your bags because we’re leaving tomorrow for a month-long international vacation, where would you want to go first?

  •  Do you think that you’ve changed since we first met? In what ways?

Tips for making conversation starters more successful

In this list, we’ve shared some interesting and engaging topics that are sure to spark conversation and help you connect with a stranger, a first date, or even an established partner on a deeper level. Here are a few final tips for making these conversations more successful:

  • Make the questions personal. If you’re meeting someone for the first time, it will be more beneficial that you say something relevant instead of throwing them a question out of the blue. For instance, if you’re meeting a stranger at the zoo, ask them about their favorite animal. If your first date is at a Greek restaurant, ask them if they’ve ever been to the Mediterranean.  

  • Be ready with answers of your own. Conversation is a two-way street, so be authentic and honest about your answers. And, be open to questions that they bring to the table, too!

  • Respect someone’s space if they don’t want to respond. Whether you’re talking to a guy online or meeting through mutual friends, you might find that they’re simply not as invested in the conversation as you. Or, maybe that guy that you’ve been seeing at the gym or coffee shop is giving off the vibe that they don’t really want to talk. Don’t take it personally, and don’t push them to engage if they’re not willingly doing so.

You can be bold with these conversation starters to use with a guy!

It’s time to stop feeling disappointed that the guy you’re interested in hasn’t taken the leap to start a conversation with you. With the right icebreakers, this can be your moment to be brave and start making the kinds of conversations you want to have!

So, which of these 50 conversation starters with a guy is going in your arsenal?

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