16 Conversation Starters With a Guy

By on September 26, 2014

So, there you are, gazing across the room/lecture hall/bar/gym/ wherever, at the most jaw-droppingly yummy guy you’ve ever seen. Just staring at him makes you feel warm and fuzzy inside. You just KNOW you were meant to be together. So what do you do now? Do you stay quiet, and secretly admire from afar? Or are you ballsy enough to put yourself out there and start a conversation?

Don’t worry if the thought of this makes you want to run and hide. All of us are tongue-tied when we first talk to a guy we like. Even though men are the ones who are traditionally supposed to start a conversation, they are just as terrified as we are. In fact, your dream guy could be secretly looking at YOU out of the corner of his eye, wondering how on earth HE can get to talk to YOU!

So follow these simple tips for some fun conversation starters, and get that cutie out of your dreams, and into your life!

1. Drop Something

The classic romantic ploy; walk in front of him and drop a book, your scarf, your watch… anything that will attract his attention. Unless he’s a total jerk, he’ll stop, pick it up and hand it to you. You say “thanks” and take it from there! Easy peasy.

2. Get a Friend to Help

Used by girls for generations, this method of making an introduction takes the stress off you and leaves no doubt in the guy’s mind that you’re interested. Use this when you’re out with your girlfriends and notice a guy on another table or across the room. He’ll probably have noticed you and your friends looking at him and whispering, so he’ll know something is up. Send your girlfriend over to tell him you like him, while you stay put, smiling at him and looking cute. If he has any interest at all, he’ll take the bait and come on over to you. This is where the rest of your girlfriends helpfully disappear, leaving you and him alone to get acquainted.

3. Almost Fall


Basically, this move involves faking an “almost fall”, where you have to grab onto him to stop yourself from falling down. I recommend you practise this move with a girlfriend first, as you don’t want to really fall and possibly hurt yourself or make yourself just look like a klutz. High heels are a benefit, as you can angle your foot a little and it looks like you twisted your ankle. He will of course, help you up (assuming he’s a gentleman) and ask if you’re okay. Thank him sweetly, and give him a sincere compliment such as “Wow, you have such beautiful blue eyes!” Hopefully he’ll return the compliment, and Zing, there goes the spark between you!

4. Ask him a Question

Strangers ask us questions all the time, and the basic rules of politeness demand that we respond. Use this to your advantage, and approach the guy you like with a simple question such as “What time is it?” or something more specific to the location such as “Do you know what time the train to Smithville leaves?” He’ll give the standard response of course, but the ice has been broken and you are now free to continue the conversation with other comments or observations. Even if you walk away this time, next time you see him you’ll be able to smile and wave in recognition, and you’ll be buddies before you know it.

5. Ask for Help


I know that the feminists out there will sigh and roll their eyes when they read this, but the truth is guys love to feel manly and knowledgeable. A little Scarlett O’Hara play-acting can never hurt when starting a conversation with a guy. Asking for help to carry something heavy is the obvious, but you can also ask for his opinion on something. Electronics are great for this, and hanging out at the Apple Store or your local Best Buy will find you a good-looking nerd who can fix your computer and rub your toes at night!

6. Ask for Directions

Like the previous two suggestions, this is a commonly accepted way to approach a complete stranger. You don’t have to really be lost, just pretend! This works well in the mall, as you can simply ask if he knows where a specific store is. The aim here is to talk him into actually guiding you to your destination, and the conversation will flow naturally as you walk together.  Clever, huh?

7. Talk to his Pet


Guys with pets are just so adorable! Although it’s considered weird to strike up a conversation with a complete stranger without any reason, it is perfectly acceptable to pet a dog and tell him what a cute puppy he is. This will lead to a conversation with the dog’s owner, and has the added benefit of giving you a ready-made topic to discuss.

8. Fake a Wrong Number

If you can get his phone number, call and ask for someone else – just make up a name. When he says “sorry wrong number” pretend to recognize his voice and say “is this (his name)?” Of course he’ll say yes, you say who you are, and follow up with a comment or question. Something like “Wow, how random. I meant to call (fake name) and I misdialed you. That’s so weird. Must be fate, huh?” Bingo – you’re talking.

9. Take Something of his by “Mistake”


Oops! You picked up something of his instead of yours, so of course you have to apologize and give it back, which gives you an excuse to open a conversation. Order right after him in the coffee shop, and pick up his coffee instead of yours. He’ll probably be asking you for it before you even get a chance to say anything to him! Please don’t take a sip from his cup though – that would be just gross. Save swapping spit for later! This can work in a class as well, take his completed paper from the pile along with yours, and then pretend to notice, look around and go over to hand it to him. Pretty much anything of low value that you can snag without him noticing, and then immediately give back with a pretty smile and sweet apology, will work.

10. Offer to Share your Umbrella


It’s raining, you’re walking along the street next to a good looking guy, you have an umbrella and he doesn’t. What could be more natural than to offer to share? If he thinks you’re cute he won’t pass up the opportunity to get to know you, and a brand new romance is born!  Now tell me, that isn’t a cute idea.

11. Offer him Candy


You’re sitting next to a cute guy in a public place who you’d love to say hello to. Look into your bag for some candy, gum, or even a cookie, and offer it to him. Smile and tell him that the rule about not accepting candy from strangers doesn’t count once you’re all grown-up! He’s sure to smile back and conversation will follow.  Ask him what his favorite type of candy/gum/cookie is, tell him yours, talk about sweet nothings and I promise you’ll be laughing together within minutes!

12. Blow him a Kiss


Have you been eye-flirting with a guy across the room, and want to take it a step further? Next time you catch him looking at you, blow him a kiss. It’s not exactly striking up a conversation, but I bet it’ll soon turn into one. I know this one is kinda out there, but it’s worth a shot right?

13. “Crash” your Car into his


Admittedly, this is a totally drastic move. But if all else fails, this one is guaranteed to start a conversation! Make sure you have good insurance, and make it a tiny fender bender in a parking lot. Probably best not to use this one if his car is obviously the current love of his life, and you could do your make-up in the reflection from his chrome. In that case, use the next suggestion…

14. Admire his Car/Motorbike/Boat/Four wheeler


Boys love their toys, and a compliment about his ride is guaranteed to spark his interest and start a conversation. Even better than a compliment is if you can ask a question that shows you know a little about the model or make he has, as you’re pretty certain to impress him and start a passionate discussion. He’ll probably offer you a ride, and off you go into the sunset!

15. Borrow his phone

This one is easy and will definitely work! Go up to the guy you’d like to talk to in a pretend hurry and ask him if you could borrow his phone to make an emergency call. Tell him yours just died. Call a girlfriend who’s already in on the plan, have a pretend conversation, hang up, and tell him how sweet he was to let you borrow his phone. Voila!

16. Just say “Hello!”


I asked my boyfriend what would be the best way for a girl to start a conversation with him. He looked at me like this was obvious, and said: “Just walk up to me and say hello!” D’uh! I guess it IS obvious! So ladies, breathe deeply, put on your sweetest smile and walk up to that guy! A simple hello is really all it takes sometimes.

And there you have it ladies, 16 ways to start a conversation with a guy you’re interested in. Remember most people are flattered when someone shows an interest in them, so find your inner confidence and just go for it. Good luck!


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