What to Say to a Woman in Passing


Here’s a reader’s question:

I happened to bump into her the next day in the cafe, had a brief conversation, but was really not sure what to say. You really got to help me here… as in, what do I say to her if I happen to meet her in the office cafeteria or something? As in a brief setting? If you get what I mean, because I find it pretty awkward just saying ‘sup? how you doing and stuff’ It adds to nothing.

My suggestions:

If you run into her briefly, compliment her! Tell her,

“You look very beautiful today.”


“The color of your dress really brings out your eyes.”


“You know it makes my day to see you smile. How’s your day going?”

When you see her in the cafeteria, ask her,

“What’s for lunch?”

or tell her,

“Let me treat you today.”

You can also chat her up as you’re both looking at items on the counter and ask her opinion,

“What looks good to you?”

If she says, “Oh the lasagna.” You can say,

“Oh, you like Italian?”….

Pay attention to her facial expression when you see her.

“You look like you have a lot on your mind today. How’s everything going?”


“You look like you won a million bucks. What’s going on?”

Or be silly and throw in some innuendo, some double entendres that are playful and show confidence. You gotta be bold to pull this off, something like,

“You know, _______, we really should stop meeting like this.”

It has to be kinda provocative but playful.

Do you dare? LOL

Good luck guys!

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I love thinking about the intricacies of dating, love and life. I share my tiny lessons in the hope that it helps you as you navigate the dating world.

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  1. YourDatingDiva

    I have found that what works best, is a natural conversation vs forced. The truth is, if she is interested, it doesn’t really matter what you say, she will engage. The exception to this rule is if you say something offensive or really corny, it may turn her off or seem desperate. We often forget that we are both the same animal and the similarities between men and women out weigh the differences. Put yourself in her shoes and imagine how you would react to your own “line” 🙂

    • MidoriLei


      True, if she is interested it doesn’t really matter what you say, she will engage… but I’m talking about if she’s not interested, there are ways to make her curious. I’ve gone from “would not have been interested” to “slightly curious” just by a guy being confident, charming and funny/corny, like in this situation. I guess it’s a matter of opinion.

      I don’t agree that we’re the same animal. I think there are more differences than there are similarities between the sexes. sorry:( We can just agree to disagree.

  2. G2

    Hi Midori,

    In a similar context to the above reader, if a man were to walk up to a woman, look her in the eyes and say with a smile, “I find you attractive and would like to get to know you. How about we get coffee this weekend?”, what would you envision as her response, not just initially but say, later in the day? Positive or Negative? Too direct? What would be going through her mind and emotions (both good and bad)?

    That’s the subtext of how I say each of the above and it’d be fun to push it further and simply say what I mean in the very first interaction. However, it is much easier to envision in one’s own mind than in reality so a female perspective on how she’d see that interaction play out would be helpful before I try it out and I bet others guys would find that really helpful, too.


    • MidoriLei


      I like your boldness… but…

      I think in a woman’s mind she would be taken off guard, and even if she was interested, she would hesitate. She doesn’t know who you are, she doesn’t know if you are trustworthy, and she doesn’t want to come off as easy. All of these things come into play. And the way you say it: “I find you attractive and would like to get to know you,” will make her feel you ONLY want to get to know her better because you find her attractive.

      Of course this is true, but it comes off wrong. It’s much better to build a little rapport, joke around, ask about her BEFORE you tell her you want to get to know her better. That way it doesn’t seem like you’re just asking for shallow reasons. Also when you say, “HOw about we get coffee this weekend?” It doesn’t show a pursuit on your part. It is much more attractive when it is a real invitation and an offer to “treat” her. See the difference with this?

      “I’d love to take you out for coffee this weekend. Are you free Saturday? I know a really great coffee house around the corner.”

      1. It shows your desire (I’d love to take you out)
      2. It shows you are planning to pay for the date.
      3. It shows risk, not just you saying you want her to “come along,” the way your “How about we get coffee this weekend” comes across.
      4. It details logistics so she starts thinking of concrete plans. (Are you free Saturday?- day. I know a really great coffee house around the corner- place)
      5. It shows that you thought things out more thoroughly since you already have thought of the day and place. You cared enough to make a plan. A man with a plan is HOT.

      The approach is not too direct. Men typically fail on the side of not being direct enough! Direct is good!!!

      Here’s how one person approached me and I loved it!

  3. Katie Martin

    I think these are really reasonable suggestions for striking up a conversation. Often when first interacting with a woman men are often either way too up front and obnoxious or they give no hint they are interested at all. These tips on just how to get yourself into a conversation are great ways to get her attention without making her feel uncomfortable or forced to interact. It is very important to pay attention to her body language and eye contact cues though. And your step by step explanation here in the comments is fantastic! You should post just that sometime, because obviously guys are not getting it. LOL!

  4. Megan Jones

    I agree with YourDatingDiva. What makes you interested when someone talks to you? I think if you put out what you like, you are going to attract someone who you are compatible with. If you love corny jokes, then by all means use them! If someone doesn’t respond, you probably aren’t that compatible anyway. Be yourself and you will attract someone who likes you for you, not someone you are pretending to be.

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