7 ways to start a conversation with a guy (without being awkward)

Wait. You wanna talk to a guy? Do you know how easy that is!?  I know because I’m a guy.  OK, if you want to talk to a Brad Pitt-level boy — you know, someone …

Wait. You wanna talk to a guy?

Do you know how easy that is!? 

I know because I’m a guy. 

OK, if you want to talk to a Brad Pitt-level boy — you know, someone with a tornado-proof hairdo, sharply pressed suit, and “I know I’m hot” halo — that’s a whole different story. 

But still, most guys don’t get approached like women do… 

which means you have a fairly high success rate if you chat up a guy. 

He will be flattered and even flabbergasted. 

OK, knowing that the odds are on your side is great, but how do you actually walk up to him and spark a conversation? 

Here are a few tips: 

Make sure that he’s alone and relaxed 

If the guy is with someone else or a group of friends, it’s hard to have a proper conversation without the third party eavesdropping. Not to mention the anxiety that comes with the additional attention!

And, if he’s in the middle of something, or if he seems stressed, it wouldn’t be the best time to talk with him. Find a different time and day, or just move on to other guys. 

Approach him during the day

This isn’t to say you can’t talk to a guy at night. But the odds of him thinking “am I gonna get laid” will be much higher. (If that’s what you want though, go for it sister!!)  

Daytime conversations tend to be neutral in sexual intent, which helps you get to know him first before the hanky-panky. 

Make small talk  

As much as you’re interested in him, it’s important to get a better sense of his personality. Well, you might like how he looks, but not how he talks. 

This is where small talk is helpful: it helps you build rapport without going too personal just yet. Here’s a list of conversation starters that are suitable for small talk:

Conversation starters with new friends, or people you just met

Tell him that he’s cute

No need to beat around the bush. Instead, directly express your interest, which in turn triggers their interest in you too. 

This is known as the reciprocity principle, which states that “attraction breeds attraction“. In layman’s terms, we like people who we know like us. 

Keep the compliment simple — think of it as a stamp of your intent, rather than a test of your language acrobatics. For example: 

  • You’re cute!  
  • You’re handsome.  
  • I find you attractive.
  • You caught my eye… 

Flirt with your eyes 

If you’re too shy to verbally compliment him, put your “hey hottie” gaze to work instead. Eye contact can often be the easiest way to flirt, since no words are needed, and there’s no physical contact. 

Just make sure that he actually notices your gaze, so that your effort doesn’t go to waste. A few things to keep in mind: 

  • Look at him for at least 1-2 seconds (three is the max
  • Take off your sunglasses if you’re wearing them  
  • Sit or stand closer to him, ideally in his line of sight
  • Smile!

While signaling your interest is important, do pay attention if he reciprocates or not. If he looks back at you — for the same amount of time and more — you’re one lucky gal. In a study, participants who mutually gazed at each other reported the highest degree of attraction than other participants.

Be a familiar face in his life 

The more frequently you see someone in person, the more likely they will find you likable. This is the power of the mere-exposure effect. Dr. Patrick Keelan, a psychologist, explains

“[The mere exposure effect] is a response built into us as a result of our evolutionary past in which people were more likely to survive if they approached people and other creatures only once they had determined that they were non-threatening… once you see the same people more often, liking will tend to naturally increase as you come to see each other as ‘non-threatening.’”

But what does that mean for you? Let me explain…

  •  If you’re at work, chat up your male colleagues… the risk of office romance be damned!  
  • If you go to the same cafe multiple times a week, talk to the cute barista as well as the other regulars. 
  • If you love working out, join a gym and participate in the weekly training as devoutly as possible… you get the point.

By being a familiar presence around him, you also enjoy an underrated benefit: being able to get to know him over multiple conversations, rather than rushing the dance of attraction and making him feel pressured (yes guys can feel pressured too… it turns out that we are humans just like you)

How to text a guy 

OK, if you got the guy’s number… What’s next? Apart from calling and asking him out, you’re probably thinking about texting him. 

Rather than engaging in awkward, boring back-and-forths, here’s how to increase your odds of a fun, meaningful text conversation:

    • See what medium of communication he prefers. Some guys like me absolutely love texting, others would prefer voice messaging or calling instead. Ask him about his preferences upfront, so that you don’t jump to the conclusion that he’s not into you.
    • Text as much/little as he does. When one person is writing a lot more than the other, it can lead to imbalanced relationship dynamics. You might feel the urge to share or ask more than he does, accept your desire and give him space to respond as he wants. (Now, if he hasn’t responded in a while, data shows that a second text is OK if it’s a few hours after the first text at least. I personally recommend 24-48 hours.) 
    • Ask an interesting question now and then. Going with the flow is good, but it’s easy to slip into the mundane, for example “hi what you’re doing” — “not much” –“OK”. The right question can transform the entire text conversation, and even open up the doors for deeper sharing in the future. See: Conversation starters categorized by topic
    • Save controversial/emotional topics for in-person conversations (if possible). When it comes to expressing feelings or discussing thorny issues, there’s only so much that emoticons — or walls or text — can do. Heather Wilson, a licensed counselor, said: “If you’re planning on sharing something that could be construed as negative or offensive, it’s best to do so in person. This way, you can gauge the other person’s reaction and explain your feelings more clearly.”
  • Invite him to meet. What you don’t want is an endless stream of flirty text messages… but no in-person dates. Sometimes, the girl’s gotta take the lead (we are in the age of feminism, after all!) 

What to do if he’s not into you 

Despite your best efforts, the conversation just isn’t flowing… What do you do? Rather than blaming him or yourself — or trying harder to make things work —  consider ending the conversation instead. Here’s how to do it politely.

And more importantly, accept the disappointment as is, without spinning it into a story of why you’re unattractive. Here’s what Juliana Breines, a psychologist, wrote

couldn’t you frame the “He’s just not that into me” message in gentler terms, like, “Maybe he’s not the guy for me” or “I deserve someone who treats me well,” or even “Oh well, I guess he just doesn’t realize how awesome I am”?

PS: Now, if you’ve got the guy’s number (congrats), and you want to spark a text conversation — with less awkward back-and-forths — my friend C.B. Daniels has a lovely list of 25 questions to ask him over text. Good luck!!

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