How to Approach a Guy: 16 Sneaky Tips to Help You Start the Conversation

Gone are the days when you had to wait for a guy to approach you. You’re an empowered woman…you just need to know how to approach a guy and you’ll do it.

Maybe you didn’t make the first move when you were last single, but you’re ready to try something new at this point in your life. Still, if you’re struggling with the idea of approaching a guy because you feel like you’ll come on too strong, let me help you shift your mindset.

Don’t think of approaching a man you’re interested in like you’re “hitting on a guy.”  Instead, see it as you being “extremely social.” This removes all of the pressure you might otherwise put on yourself!

Oh, and one more thing before we dive in. Don’t forget how terrified guys are of approaching women! They fear rejection. But by you learning how to approach a guy, you give him a “window of opportunity” to then start pursuing you. And there’s no rule that says just because you do the initial approaching that he doesn’t have to do some work too. Once you catch his attention, if he’s interested, he’ll need to woo you properly.

16 Tips on How to Approach a Guy

You might try all of the following suggestions, but find that one or two become your go-to moves because you’re comfortable with doing them (and they always brings success!). Or you might switch it up every time you see an attractive man just to keep things interesting. Either way, the more you practice, the more confident you’ll become at approaching men.

1. Ask to Borrow the Salt

My favorite suggestions on this list are the ones that you could do to anyone, whether it was a cute guy or not. Who’s going to think you’re hitting on him just because you ask to borrow the salt from his table at a restaurant?? (Just make sure there isn’t a salt shaker sitting on your table!)

As he’s reaching to get the salt, do a quick scan of the situation to find something to start a conversation about. You could ask how he likes his steak or compliment him. Use the “I need salt” excuse as a foot in the door so that you don’t simply turn back around and shake sodium on your meal, and that ends that opportunity.

2. Ask What He’s Drinking

I always tell my coaching clients to sit at the bar if they want to meet someone. It’s hard to strike up a conversation when you’re at a table, but when you’re sitting right next to a good-looking guy, it’s much easier.

Particularly if you haven’t ordered your drink yet, you can ask what he’s drinking. If it sounds good, ask more about it. If he’s interested, he’ll let you taste it. Use the opportunity to talk about the merits of different beers or liquors, then make yourself comfortable in the seat next to his.

The worst that can happen is that he’s not interested or his girlfriend returns from the bathroom (check to see if there’s a purse in the chair next to him first!). But even then, at least you got a good drink recommendation.

3. Pretend Like You Know Him

Okay, it may be a little devious, but what’s the harm in pretending like the guy looks familiar? It’ll get him to open up as he tries to figure out how you might know him.

“Do you go to the gym down the street? Or maybe you know my cousin Beth?”

Eventually, he’ll have to give up the guessing game and just have a conversation with you. If you’re feeling extra sassy, you could even confess that you made it up as an excuse to talk to him.

4. Brush By Him on the Way to the Restroom

Sam is sitting on a stool at the bar when a beautiful woman (you) lightly brushes his backside as she passes. It was an accident, he thinks, until he looks up and sees your smiling face. Maybe it was no accident after all…

Obviously, this is a weird thing to do if there’s plenty of space on the way to the ladies’ room…or if he’s not sitting anywhere near the path there! But in a crowded bar, it’s the perfect excuse. If you bump him slightly, you now have an excuse to talk to him and apologize.

5. Stay Centrally Located

The booth in the corner might be your favorite seat at your local restaurant, but this position won’t help you succeed at how to approach a guy. Instead, stay in the center of the room wherever you go. When you’re centrally located, you’re more likely to get the attention of males in the room, and this will increase odds that a guy will come talk to you.

If you’re with a group of friends, sit on the outside, rather than flanked by your ladies, to make it a little less intimidating for a man to approach you.

6. Ask the Score of the Game

Whether you’re into sports or not, being in a sports bar during a game is a great opportunity to meet men. This is another good time to sit at the bar rather than at a table. That simple question, “what’s the score?” will be enough to get him to peel his eyes away from the television to be swept away by you. If you’re genuinely into the game, you can talk stats and players. If you’re clueless, ask questions to make him feel like he has something to teach you.

Don’t be too offended if he spends more time watching the game than flirting with you; he came to the bar with one intent for the evening, while you came for another. If you think he’s into you, stick around and see what happens at halftime.

7. Talk to His Friend First

If, as you’re learning how to approach a guy, you’re not quite ready to walk up to a man you’ve been eyeing, try this: talk to his friend(s) first. You can use any of the techniques in this list geared toward them. Ask the friend for a salt shaker. Tell him he looks familiar. Get comfortable talking to the friend and then open your conversation up to include the object of your desire.

Nobody likes to be ignored when their friend is flirting with someone else, so this strategy makes sure to include the friend as well as use that conversation as a jumping off point to talk to the guy you’re crushing on.

8. Simply Smile and Say Hello

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Not every one of these tips on how to approach a guy requires strategic planning. The simplest technique is to just smile at him and say hello. Introduce yourself and ask his name. Again, this isn’t hitting on him; you’re just being friendly.

Pay attention to his reaction. You can easily tell if he’s interested in you; watch his body language. If he turns toward you, that’s an excellent sign. If he leans in toward you, even better. If he smiles while he’s talking and even asks you questions, he’s definitely into you.

9. Compliment Him

Everybody — and I mean everybody likes being complimented. It’s a great way to put someone at ease, especially because when your gorgeous self approaches him, he might get a bit nervous!

Keep the compliment simple. Focus on:

• His clothes
• His shoes
• His hair/facial hair
• His drink or food choice

Once you’ve given the compliment and see how he responds (positively, I’m willing to bet), ask a question and get a conversation going.

10. Connect with Him on Social Media

This tip is for a man that you already know, maybe through friends or your social circle. In that case, a tip for how to approach a man might happen digitally, through social media.

You can follow him on Instagram, but chances are he’ll never notice if you do. Facebook is a better channel to get his attention because he has to approve the friend request. Once you’re connected, be sure to comment on his status updates to stay on his radar. Maybe you can share a post that reminds you of him (and say just that), like a video of a basketful of sloths (he loves sloths).

11. Ask Him a Question

The sky’s the limit with this tip. You can ask him about the weather, what he’s listening to on his headphones, what he ordered…

You could even stump him by asking him a question that completely takes him off guard.

“Would you rather never eat your favorite food again and be rich or be completely broke and be able to eat it?”

“If your house was on fire, what’s the one thing you would take?”

“What’s your dream vacation?”

No man expects a woman to approach him asking these types of questions, so you’ll instantly get his attention.

12. Order a Drink for Him

You’ve seen this move in romcoms, but it’s usually the dude sending a drink over to a pretty lady. You’re empowered, so flip the script and send one to him.

When the server brings him his drink, be ready with a smile and a wave from across the room. I guarantee he will get up and walk over to you. Classy!

13. Ask a Friend to Introduce You

So you find out that the guy you are lusting after at a party is a coworker of your best friend. This is one of the easiest ways to learn how to approach a man because you’ve already got an in: your friend.

Grill her to find out what she knows about him. Obviously, start by finding out if he’s available and straight, but then see what she knows about his interests. She can help you find common ground. Maybe you both love hiking. She can use that commonality when she introduces you to get the conversation started. From there, it’s up to you to dazzle.

14. Make a Face at Him

Most of the tips I’ve given so far are pretty standard in terms of how men and women meet in public places. But maybe you’re extra spunky and want to stand out from everyone else who’s ever flirted with this guy. Try this: stick your tongue out at him or make a funny face, then smile. He will be so thrown off that he’ll want to know why you did it. Your reply might be something like:

“I assume you’ve heard every pickup line in the book, so I wanted to try something different to get your attention.”

In fact, he probably hasn’t heard that many pickup lines, but he’ll be flattered that you think so.

15. Beckon Him with Your Finger

If you want to know how to approach a guy, sometimes you’ve got to be bold, like in #14. Another bold move: if the two of you are making lingering eye contact across the room for a while, just smile and beckon him with your finger.

You: [smile and beckon]

Him: [looks behind him] “Who me?”

You: “Yes, you. Get over here!”

16. Dance By Yourself

Let me just say: if you’re at a dance club and you are surrounded by your besties, there’s no way a man is entering that shark pit. It’s too darn intimidating. So if you see a man looking your way, separate yourself from the pack and dance alone. It’s much easier for him to approach you, and if you smile and toss your hair in his direction (or maybe use that finger to beckon him) he’ll understand that you want him to dance with you.

What to Do Once You Approach

You’ve already done the hard work by succeeding with your plan on how to approach a guy…but now what? You’ve mesmerized him with your flirting skills…but what do you do with him now?

Most women I’ve coached find that once they get over the initial fear of rejection and see that the man responds positively to their efforts to get his attention, that the rest is easy. If you’re a good fit with this guy, the conversation should flow easily. If not, well, he might not be right for you.

Just don’t put pressure on yourself. The worst case is that you have a short conversation with the guy, realize you’re not compatible (maybe when he boasts about his massive gun collection), then walk away. No harm, no foul.

The best case is that you hit it off. You laugh and talk for hours. Your friends leave you there so you can keep talking. He gets your number. He calls. You go out and live happily ever after…er, or something in between these two situations.

Regardless of what happens, you’re simply sharpening your dating skills, which can be valuable, particularly if you’ve been out of the game for a while. So even if it doesn’t work out, you’re getting some value out of the situation.

Conclusion:

It may take a few tries before you can psych yourself up enough to learn how to approach a guy with confidence and ease, but you’ll get there. I understand that your self-esteem might have taken a tumble due to past relationships, but there’s no better time to rebuild it than right now!

Test out these strategies. See what works for you, and what you’re most comfortable with. While I do encourage you to push beyond your comfort zone, I don’t want you to try any strategy that gives you outright anxiety. Dating should be fun! Keep that in mind.