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How to Start a Conversation With a Guy: 9 Golden Tips

In this article we are going to talk in detail about how to start a conversation with a guy.

While I’m a fan of binge-watching Bridgerton and have read all the books by Julia Quinn, I’m happy to report that these days, we don’t have to wait around for a man to make a move or to be introduced by a mutual acquaintance.

Some might lament the end of old-fashioned courtship, but there are some pretty significant advantages to modern dating. 

For instance, money isn’t the primary motivator for lasting relationships as it might once have been.

Women actually have rights and aren’t given away by their fathers in a deal that involves cash and livestock.

Social status isn’t seen as the ultimate barrier in relationships, and no one is really rushing to see you married before you’re of legal age to vote. 

Modern dating has its downsides, too.

Dating apps tend to be more frustrating than fun, ghosting seems to be more prevalent than kindness and honesty, and sometimes men want to “hang out” rather than asking us on an actual date. 

But the good news is that women can ask out men or whoever they’re interested in without needing an introduction, parental permission, or attending a multitude of fancy dress balls.

Okay, that last one makes me a little sad now that I think about it. 

You might not have an actual dance card to fill, but if you see a guy you like, you might wonder how to break the ice and get to know him.

There are some simple ways to do this. 

How to Start a Conversation with a Guy: 9 Golden Tips

1. Say Hello

Have you tried saying hello? It’s the simplest way to start a conversation with a guy. This option works best in person. Just say hi and see if he’s responsive.

If you get a hello in return and then he looks away, looks down at his phone, or otherwise doesn’t engage further, he’s not interested in talking to you. 

Don’t take it personally. He could have a wife hidden in his attic, be in a serious and happy relationship, or just might not be returning your interest.

Opening with something simple could tell you a lot. If he seems receptive, it could lead to an introduction and conversation.

This doesn’t work as well online or on dating apps. A “hello” by itself might not initiate a real conversation, and it might get lost in the volume of boring messages they’re receiving.

You might have to make more of an effort to communicate your personality when you start a conversation online, but a simple “hi, how are you” could actually work if you want to chat up the cute guy you see in line at the coffee shop.

2. Lead with Humor

Humor is always a hit — if you’re good at being funny on the fly. Just make sure you don’t lead with a joke that could be considered offensive. If you’re not sure, it’s probably best to err on the side of caution. 

Humor doesn’t have to be an actual joke either.

A funny observation can break the ice. Even being able to laugh at yourself in an awkward encounter can ease the tension and allow for an introduction.

So, if you get nervous and spill your coffee all over yourself, you can handle it with a quick quip and flirty smile. 

Recommended read: 10 Best Conversation Starters for Tinder (or Bumble) That Will Help You Stand Out

3. Try a Compliment

Compliments are an all-around good idea when they’re appropriate. You’ll need to read the room.

Complimenting the fit of his grey sweatpants isn’t on the same level as telling him you like his eyes or that you really admire his work. Flatter rather than objectify.

If you don’t know the difference, you might want to skip this tip and try something else.

A compliment doesn’t have to be physical either. You can compliment anything you notice about him that you like. Just make sure to read his cues.

If he seems uncomfortable, don’t continue. Just move along. If he’s receptive to it, you could settle in for a full flirtation.

The online version of this is to leave a comment under a photo or post. You could even send him a direct message to let him know what you like.

Obviously, if he’s in a relationship of any kind, don’t do this, but if he’s single and by all appearances free to mingle, a compliment could be flattering and make his day even if he doesn’t reciprocate your interest. 

4. Make an Observation

If you don’t have a clue where to start, share an observation. For instance, if you’re both hanging out at the same place, comment on something. Anything.

How slow the line is, how much you like a particular coffee there, even the weather. It gives him an opening. If he’s interested, he’ll take it.

This is so much easier online. You can look at a few photos and find something to comment on. In his vacation photos, you can mention how much fun an activity looks.

Simply use your observational skills as a way to strike up a conversation. He’ll either acknowledge your comment or he won’t, but you can’t say you didn’t try.

5. Search for Common Ground

One of the best ways to start a conversation with a guy – and keep it going – is to figure out common ground.

If you’re both watching your pups play at the dog park, talking about your pets is a great introduction.

You can assume he’s a dog lover, and you likely are, too, if you’re hanging around a park with your pup. So… use it. 

You might not be able to immediately see common ground, but sometimes you can see when you don’t share interests.

I might steer clear of someone wearing a Trump hat, but if I see a BLM logo, I could see an opening for a conversation. 

It’s as simple as letting them know you like the things they do. Their vintage band shirt might just be something they found and wear without being a fan, but it’s possible that they like the music you do.

Time to find out.

Recommended read: 12 Quality Conversation Starters That Make You Instantly Charming

6. Keep It Friendly

Of course, you can always complain about something or someone. It’s a conversational opening for sure. But is it a good one? 

Keep any introduction friendly.

Complaining might form an easy bond, but it’s not exactly a stable one. Instead of finding something to fuss about, think about a more positive way to start a conversation. 

Why does this matter? An unhealthy start might not be an auspicious one.

Hey, if you’re vibe tends to be dark, you might like to start a friendship or relationship with snark, sarcasm, or dark humor, but make sure the vibe you’re sending out is the same one you want to attract. 

7. Make Eye Contact and Smile

If you’re shy, it might be hard to do this — but it might be even harder to find the words to say hello. If you see someone you like, try making eye contact and smiling.

This might feel awkward initially, but it might help you determine if he’s feeling the same vibes you are.

Staring and smiling can get creepy if you do it too long, so don’t make it awkward. Instead, start out with eye contact and a smile.

If he returns it, you could say hello or try another conversation opener. 

Recommended read: How to Tell a Guy You Like Him: 7 Clever Ways to Do It

8. Ask Him for His Assistance

One of the best ways to start a conversation with a guy is asking him to help you.

Some men like to feel strong and needed. If you’re a shortie like I am, you might want to ask for help reaching a top shelf at the store.

Of course, if you’re also an independent woman like I am, you might find it a cringe experience to ask for help at any time, much less to make an introduction.

In this case, you could always ask for directions, ask for the time, or find some other way of letting him help that won’t offend your feminist sensibilities.

After all, you might not actually need the help. You might just want the excuse to talk to him. 

I once had a crush show me how to lift weights even though I’d been lifting off and on since I was a teenager.

Did I need help learning, or did I want to spend more time with him and maybe watch him flex? You know the answer already.

Of course, I told him this was the real reason later, and we laughed about it. 

9. Interact on Social Media

If you’re shy or you’re just testing the waters, one of the easiest ways to strike up a conversation is to interact with his social media content.

You can like his pictures and stories all day, but that’s unlikely to start a conversation and may come across as stalker-level behavior. Instead, comment on his photos or stories. 

Not only does this show your engagement and interest, but it also gives him a chance to respond if he’s interested.

Once again, you’ll want to keep this friendly so it’s best to avoid trying to argue with his political posts or musical preferences. Find something you like and comment on that. It’s an opening.

Will he take it?

Recommended read: Follow-Up Questions: The Key to Have Meaningful Conversations

Some Reminders for the Conversation

Conversations Should Be Mutual

Just keep in mind that you can’t single-handedly carry the conversation. If you’re doing most of the work of being interesting, you might need to accept that he’s just not that into you and move on.

If he’s not a good conversationalist, you might want to consider that if you’re interested in being his friend or dating him.

Keep It Real

Don’t be the version of you that you think he wants. Be yourself. It’s common advice, but it’s so important. If you give him a fake version of you, real you is going to come out at some point.

Don’t you want him to love you for you now rather than be disappointed later that you weren’t who you said you were?

Don’t Assume

Never assume anything. Don’t assume you know who he is or what he wants. Don’t superimpose what you want over him. Instead, pay attention. Be curious. Be interested.

If you’re not sure of something, just ask. Never assume or take anything for granted.

Are you ready to strike up a conversation? Throw on your favorite music to get into the vibe and then get ready. 

Just remember that if he’s not into you, it’s not personal.

But you’ll never know unless you give it a try.

Photo by Josh Felise on Unsplash

The Truly Charming