How To Approach Men In The Real World In A Feminine Way

Sure, we want guys to pursue us, but that doesn’t mean we can’t ever make the first move.

By Keelia Clarkson3 min read
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You’ve spotted a guy across the room. Maybe you locked eyes with him from across the bar, noticed him sitting a few pews over, or your schedules are magically aligned to the point where you see him every morning on the subway. Whatever the circumstances, and however many times you’ve come across him, you can’t help but take note of him and like him.

Despite dropping him what you feel are more than a few strong hints (meeting his gaze, smiling softly, or angling your body toward him) and picking up what you’re pretty sure are signs of interest from him, he hasn’t made a move. You can only guess as to why this is. Maybe he’s not actually interested in you, or maybe he’s shy, or maybe he’s worried about coming off like a creep

Either way, you feel caught – you don’t want to pass up the opportunity to get to know him and wonder if you just missed out on an amazing guy, but you also don’t want to totally take the lead. You want to find a way to approach him first – but in a feminine way. You still want to feel like the “girl” in this scenario, the one who’s sought after, chased, and pursued.

You still want him to take the lead, but you’re realizing it might be necessary to give him a little encouragement in the right direction. But how? How can you approach a guy in the real world in a “feminine” way? How can you drop the hanky, so to speak, without feeling like you’re the only one doing the pursuing?

Give Him Your Number

Would you prefer for him to be the one to initiate exchanging numbers, for him to ask you? Of course. But it’s fair to say that many men today are nervous about approaching a woman out in public, fearing their innocent interest may be perceived as creepy. And if he’s mostly concerned about not making you uncomfortable, he might just choose to play it safe and not approach you at all.

Give him a nudge and leave no doubt in his mind that you’re interested by writing your number down on a piece of paper (and if you’re feeling extra adventurous, maybe even include a short, flirty note, like “Hey, you’re cute. Call me.”), confidently striding over, and handing it to him – this way, you’re essentially handing him the ball to hit into your court. This still allows him to be the initiator, by being the one to reach out and text you, while offering him peace of mind knowing that he’s not barking up a tree that wants to be left alone.

Ask Him If He’s Single

Yes, it’s undoubtedly bold to come right out and ask him if he’s single, but it’s also a real time-saver – one that keeps you from getting too caught up in a whirlwind of emotions for a guy who ends up already being taken. While this approach certainly isn’t every woman’s cup of tea and won’t suit all personality types, you can’t deny its efficiency. You’ll know instantaneously whether or not there might be anything between you.

After making eye contact with him a few times, walk right up to him, and with a soft smile, say something like, “Hey, I couldn’t help but notice you when I was sitting over there. Are you single by any chance?” This is a straightforward move that will immediately let him know any interest he shows will be reciprocated, which will embolden him to keep the ball rolling and start flirting with you.

Ask Him a Conversation-Starting Question

Sometimes, just getting the conversation started is the hardest part. If he knew without a shadow of a doubt that you’d be responsive to his bids, he likely would have already opened up a conversation – but if this isn’t the case, why not just do that part for him? Why not be the one to start the conversation before allowing him to take the lead?

There are countless simple conversation starters to use, whatever the circumstances might be. Ask him what he’s drinking, or what he’s reading, or even for the time. The point isn’t to have the world’s wittiest conversation starter, but simply to open up a conversation that will give him the green light to keep on chatting you up.

Give Him a Compliment

We ladies aren’t the only ones who enjoy a compliment. And considering men get far fewer of them than women do, offering him a compliment right off the bat will help you make a lovely first impression and make him like you all the more. Not to mention, it will instantly make him feel great about himself, and there’s no better way to begin a conversation than by making the other person feel like a million bucks.

Zero in on something about him before approaching him. Maybe you really like his smile, or he looks good in that jacket, or his hair looks nice. Tell him exactly why you couldn’t help but notice him. Think of something specific to compliment him on rather than simply saying, “You look good.” This will prompt him to return the compliment – and just like that, you’ll have sparked a connection without being the one doing the chasing.

Ask Him for a Recommendation 

While this tip is specifically suited for coffee shops, restaurants, or bars, it’s one of the best, most natural ways to approach a guy without it feeling like you’re too obviously hitting on him (it also saves you from feeling embarrassed if it quickly becomes obvious that he’s not interested in you). Asking for his opinion is sure to flatter him.

After catching his eye a couple of times, smile at him and approach him, asking something along the lines of “Have you been here before? I can’t decide between the cold brew and the chai latte. What do you think?” If he seems interested and gives a genuine response to your question, take his advice. Even if the conversation doesn’t continue at that very moment, this allows you the opportunity to pick things back up a while later, thanking him for such a wonderful recommendation.

Closing Thoughts

Whether the guy you’ve got your eye on is shy, doesn’t want to come off badly, or is too nervous to flirt with you first, there’s always a way you can approach him without feeling like you’re the sole initiator.

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