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You have to admire the tenacious nature of men: for them, it’s always “worth a shot” when it comes to hitting on women. Even women they’ve been your friend for years! Don’t think your safe from advances from your male friends. Here’s how to nudge them gently back into the friends zone where they belong.

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Reel in the smiles

Unfortunately, men see what they want to see. And even though until now, your smiles and laughter were interpreted as platonic, now that your male friend wants to be more than friends, he’ll see them as flirty. It will feel awkward at first since you’re so used to being friendly, but for a while you’ll have to smile a little less at your smitten friend, and laugh at his jokes with less enthusiasm.

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Offer to introduce him to a friend

Take on the role of matchmaker for him—rigorously. When you’re at a bar, point out girls he should talk to. Even go to a girl without his permission and say, “That guy over there thinks you’re cute and wants to say hi.”

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Talk about other guys

Like, a lot. If you have to, pretend to be super into a guy that you only feel luke-warm about. When he’s around and you get a text from your sister, pretend it’s a flirty text from a guy.

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Talk about some other guy who’s hitting on a friend

Tell a story—even if it’s made up—about a female friend of yours who is dealing with a male friend hitting on her. Act repulsed at the story.

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Stop all one-on-one hang out’s

Remember, he is interpreting things as he wants. So whereas before it might have been totally commonplace for the two of you to order takeout and watch a movie at your place alone, now he sees that as you asking for a date. And he will pounce! If he asks for one-on-one time, you’re “busy.” But feel free to continue to include him on group hang-out’s.

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Don’t drive with him

To sneak in alone time, the guy will try to at least carpool with you to group hang-out’s. For as long as you have to, make up reasons why you can’t (you’re coming from another part of town, you have to go somewhere else after so you need your own car etc.)

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Be a little cruel

When the guy says something blatantly flirtatious, respond with sarcasm or a cold stare. Show that you find his behavior ridiculous. If he wants, that’s his chance to pretend he was “just kidding.” Either way, he’ll know the idea of you two being more than friends provokes a negative reaction out of you.

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Act disinterested in his conversation

Another tactic for when the guy is flirting is simply looking away, remaining silent for a few seconds, and changing the subject when you turn back to him. This is almost better than making a sarcastic comment or even laughing it off, because it says you don’t even acknowledge his advances.

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High-five’s and fist-pounds

These are your best ally as far as awkward physical interactions go with the guy. If you used to hug when you’d see each other, now that he’s being flirty, immediately raise your hand for a high five or stick out your fist for a fist pump when he’s still a few feet away. It will feel awkward, but it avoids any chance for his hands to linger during a hug.

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Keep conversations light

Even if in the past you’ve shared secrets and personal information with the guy, for now, stick to impersonal subjects like sports, TV shows, gossip about common friends and work.

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Don’t feed him alcohol

All your love-sick friend needs to force a public profession of his love on you is a few too many drinks so, if you can, monitor his alcohol intake.

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Slow down your text response

To create intimacy, the guy might text you every funny little thing that happens to him, or call you just to chat on his drive home from work. Before you might have felt obligated to reply immediately or take his calls but now, wait half a day to call him back or reply to a text. This will just slow down communication in general.

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Just ask him

Some guys bank on you never acknowledging their changing in behavior, so they can slowly ease into the more-than-friends zone. As if you wouldn’t notice—right. So beat him at his own game and just ask him: “Are you flirting with me? If I misread that, my bad, but if not it’s only fair you know I’m not interested in you like that.” He’ll probably deny any romantic feelings but no matter; at least he’ll stop his pursuit now.

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And if he won’t stop

If the guy won’t accept that you just want to be friends, than he was never a very good friend to begin with since his kindness only comes on the condition that you sleep with him. It will be tough but at that point, you’ll have to cut the chord.