How to Hit on a Woman (If You Want to Stay Single Forever)

It's not that women don't like to be noticed. It's not that they don't like to be found attractive. It's not even that they mind being talked to by strangers, necessarily.  

It's just that the experience of being hit on is often so awkward and fraught with ridiculousness. Actually, whether you're the one being hit on or the one attempting the hitting, I'm sure you would find little to quibble with in that last sentence. Barring rare occurrences, hitting on someone and being hit on generally provide for awkward, ridiculous stories to tell later. Although we may enjoy telling the stories, we rarely enjoy suffering through the actual events.

But never fear, men. Lest you instantly feel emotionally demoralized, I bring glad tidings: there is a way to strike up a conversation with a woman successfully, and I will eventually tip you off as to what it is.  But first, I must warn you of mistakes that will most likely keep you single for a long, long time.1

How to Hit on a Woman (If You Want to Stay Single Forever):

#1: Assume that life operates under the same parameters as a romantic comedy. Sure, some might think that it would be romantic for a handsome stranger to plunk himself down in the seat next to a woman in a waiting room and ask, "Do you know why you're here today? You're here because we were fated to meet!" But in real life, such a non sequitur at the very least will cause a woman either to come close to cracking a rib trying not to laugh at your farcical behavior or (worst case scenerio) to be genuinely creeped out. Especially if you're one of those people who doesn't believe in personal space.

#2: Assume that direct physical overtures will work. If the woman sitting next to you on the plane is shivering, do not--I repeat--do not offer to keep her warm with your own body. Even if you mean it as a joke, it is tacky. Direct physical overtures almost never work on women because women are wired to respond more readily to emotional overtures.2 So cut this sort of thing out immediately.

#3: Assume that it's in your best interests to invoke the will of the Almighty.  I'm not saying that God can't lead you to pursue a woman, even a woman that you barely know. He can, and sometimes he does. But to saddle her immediately with the information that you think God is urging you to pursue her is a message that carries with it two subtle riders: A) it took an act of God for you to notice her in the first place, and B) if she rejects you, she's going against God himself. You may mean this line as a compliment, and you may actually mean it sincerely, but to a woman, this feels like thinly-veiled spiritual blackmail. If you genuinely think that God wants you to pursue a woman, then by all means, go for it. If all goes well, tell her about God's hand in it a little bit later on.  If all does not go well, leave her alone.3 

#4: Assume that talking about ex-girlfriends/wives/flames will make you seem more desirable because these topics hint that other women have found you attractive.  It just makes you seem tacky and boastful. Cut this out.

So........ with all of these options stripped away, what alternatives are actually left to you?

First, you need to stop hitting on women and start talking to them.  As dubiously flattering as it is to be hit on from time to time, it's much more flattering for us to be found intelligent and  interesting and to feel that a man has genuinely enjoyed talking to us. Don't use pre-prepared lines. Don't use sleazy come-ons.  Don't immediately ask us if we are dating or married, as if our potential singleness is the most important precursor to your enjoying a lively conversation with us. If the woman in question does happen to be spoken for, then you will find at the end of the conversation that you have lost little more than twenty minutes or so from your seventy-year life, and that instead of feeling let-down or rejected, you may find that you may have actually gained some valuable information or secured a potential new friend.

Second, please stop using pick-up lines. Although this point is mentioned in the paragraph above, I feel that it is important enough to warrant its own clear delineation. Now, men, it should be no surprise to you that women rarely take anything that you say at face value. Women do hear the actual words that you say, but they often ascribe their own meaning to what they believe (albeit often mistakenly) are the meanings behind your words. 

For your edification, I've included below two commonly-used lines and how they scan to most women:
  • What you say: "How is it that a pretty girl like you has never been married?" What she hears: "There must be something really wrong with you if you can't find a man to marry you even though you're pretty." Also, this line implies that you think that attractiveness is the sole prerequisite to marriage. It likewise implies that you think that there is something inherently wrong with singleness. Neither one of these implications will get you very far with most of the  single women I know.
  • What you say: "You're in your thirties?! I thought you were only about seventeen!" What she hears: "I'm a middle-aged creeper who will knowingly flirt with teenagers."
See? You need to stop using lines.  If you absolutely cannot think of anything interesting to say, your best bet is to keep your mouth closed and hope that she finds you mysterious, aloof, and/or intellectually alluring.4

The best thing that you can do, men, is to talk companionably with a woman. If you find her interesting, be direct without being creepy. We're talking the kind of direct that comes out and says, "I'd like to talk to you more some time," rather than, "We were fated to meet. RESISTANCE IS FUTILE.

The truth is that swimming against the cultural tide and living as a single adult can be tricky sometimes. The least that we can do to make the exercise more effective would be to stop falling into these unintended whirlpools of flirtatious ludicrousness.5 So before strapping on your floaties and diving into the foam, remember that unless your goal is to stay single for the rest of your life, you need to stop hitting on women and start talking to them. 

1. All examples are drawn directly from life: no imagination taxed here.  They've all either happened directly to me, around me, or to friends of mine.  Truth stranger than fiction indeed.
2. I tell you this not so that you can emotionally manipulate them, but so that you can begin to understand, dimly, at least a smidgen of their motivations.  And also so that some of you will stop being such creepers.
3. Until God clues her in, of course.
4. I, for one, constantly assume that quiet people are busy thinking something very, very deep. I shudder to think what quiet people assume about me. Probably nothing, because I tell them every thought as it occurs to me in real time.
5. Really going all out on the extended swimming metaphor here. Work with me.


  1. Bravo! Photocopy this and liberally pass them out.

    Lines are good only after the relationship is established. Then, they are funny and non-creepy.

    1. Exactly! I edited out an entire digression about lines due to post length considerations, but that is a valid point. I love lines coming from people I'm already comfortable with.

  2. YUP! Just yesterday a fellow in the frozen food section approached me with the fact that my hair is just like a girl's on NCIS (?- I don't watch so I don't know if that's right). I never heard that one before. The worst was when some guy asked if I was a "dancer" at the "gentleman's club" he'd been at the night before. That was years ago and I still feel insulted when I think of it.
    I'm going on 10 years married. I never take off my ring and it's a pretty noticeable ring. A great way to stay single is to hit on faithful married women.

    1. OH dear. TACKY!

      And I've been told that men don't notice wedding rings.

  3. I prefer the expression "to chat up" rather than "to hit on" (a woman). Sounds less violent and more conversational.

    1. I prefer both the phrase and the idea of chatting up over hitting on as well. I'd much rather be chatted up. :)


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