Think Again Thursday: Pick Up Line Fail

Yesterday I was having drinks with a male friend who told me about an incident he'd had on his way back to DC. He was on a train and sitting next to an attractive woman, but he couldn't think of anything to say to strike up a conversation. He asks me, "Would it have been weird if I'd have turned to her and said, 'I've been thinking this whole time of something to say to you, but I can't come up with anything. Do you want to have a drink with me?'"

I think my jaw dropped. I said, "Yes, that would have been TOTALLY awkward! It's too over-thought." In my mind I was thinking whatever happened to "Hi" or a nice smile. I don't know; maybe I'm just too easily weirded out, but if a guy had said something like that to me, I would've been leaping out at the next stop, whether it was mine or not.

What is UP with men thinking women actually like pick-up lines? Has it ever worked on you? Some guys are still hopeful that it will. Check out this charmer from the always astute

I've had a terrible day, and it always makes me happy to see a gorgeous woman smile. Would you smile for me?

I don't know about you, but one of my biggest pet peeves is men telling me to smile. I fucking hate it. You don't know what my day has been like. I don't have to act happy for some random stranger. So why try to turn that into a pick-up line for a potential date? FAIL.

Life isn't orchestrated like pick-up lines. Life is awkward, random, fun, spontaneous, and not smooth. I'd rather have a genuine awkward hello than some line. But if you're looking to make me laugh at you, not to be mistaken with laughing with you, bring on the line. Tell me my name must be Gillette because I'm the best a man can get.*

*I got this one from my fifth grade crush.


  1. I hate it when guys ask me to smile as part of a pick up line too! I've been told my default expression is too serious, but that's just how my face is I swear haha. It seems like your friend was genuinely unable to think of something to say to her, so I don't think it would have come across like a line. If it were me I might have even agreed to go out w/him.


  2. Maybe I'm just different, or desperate, but I don't think I would view the first question as a "pick up line". It seems more like a real question and I would appreciate that MORE than a "Hey, baby, I lost my phone number, can I have yours?"

    I'm not a fan of pick-up lines at all, but I think they're just funny! If one was crafted creatively, who KNOWS what I would do. Haha.

  3. Yes even a smile would have been better. Guys are pretty clueless when it comes to women...but at least he was thinking about it and gave it some thought!

  4. I have to say it would depend on HOW a guy gave the line to me. And whether or not he was creepy.

    When I was 19 I was working at JCPenneys in catalog and this good looking guy came to pick up this GORGEOUS coat. He was nice enough, paid for his purchase and then started to walk away. Then he came back to me and said, "I'll be kicking myself if I don't say this. You're gorgeous, would you mind if I asked for your number."

    Sadly, for him, I had a boyfriend at the time. But I was incredibly flattered and it was nice to be called gorgeous by a cute guy!

    However, I also had much older, creepy guys say creepy things to me and THAT does not go over well. If I look young enough to be your daughter please don't hit on me.

  5. I totally agree! I honestly thought guys finally smartened up and stopped with the pick up lines. Smiling with a guy should be natural - if he has to ask then that's probably not a good sign lol.

  6. Haha I can't stand cheesy pick up lines too, but I think the line your friend came up with was kind of cute in an adorable dorky kind of way. It kind of shows confidence for approaching the girl while showing he's not overly arrogant at the same time by admitting he couldn't come up with anything clever. I kind of admire that and as long as he didn't look like a serial killer/rapist type of guy and I was single, I might have considered it if I was the girl :-).

  7. I completely agree on the pick up line. A simple "hi" is always the best approach. Don't plan out a conversation or try to lead it in the desired direction. If the people click, they'll click.

  8. I love all the different opinions on this one--fantastic! I think my friend wasn't thinking of delivering a line per say, but it seemed to me that he felt he HAD to have some line in order to speak to this woman. Why not just go for it instead of over thinking it? But, you're all right--he's a great guy, and maybe he would've had a shot.