For Single Guys

What to Say to a Complete Stranger When You Approach Her

This question has been asked several times. The latest is from a guy who’s interested in a girl he sees at the gym.

Here’s another reader’s question:

How would you suggest approaching women that are COMPLETE strangers? In particular what if I’m walking along and I see an attractive woman also walking. I honestly have no idea how I would initiate the conversation because in my experience if I am alone and someone walks up to me and wants to start talking to me and I’ve never seen the person before, it makes me feel awkward because I automatically think “Why is this person talking me? What does this person want from me?”

Do I need to build rapport with her or is it enough to walk up to an attractive woman and just say, “Hi. I’m Philip. I saw you standing/sitting here and you look so beautiful that I want to take you out to dinner.”

Gentlemen, gentlemen. These are great concerns. Here’s what you do:

It’s enough to ask a stranger out without building rapport, but your chances of securing the date increase with more rapport. Otherwise, she is only saying yes to her attraction to you, not to possible charm and flirtation you could throw out. If you give some rapport, she could have more to go by to see if there is “chemistry.” I wouldn’t say, “Hi, I’m philip. I saw you standing/sitting here and you look so beautiful that I want to take you out to dinner.” Although that’s the truth, it sounds like you ONLY want to take her out because she’s beautiful… Does that make sense? Also, more conversation = more time. And More time= more trust. More trust= more likely she will say yes.

Just introduce yourself like this: “Hi, I’m Philip. What’s your name?”

And then it is always good to be apologetic because you are interrupting someone’s day and being apologetic shows humility. It also gets women to trust you sooner.

Say, “Sorry this might seem really forward but if I don’t say something to you right now, I know I’ll be hitting myself on the head thinking I just let such a beautiful woman pass me by and I may never see her again.”

Do you see how it’s complimenting her indirectly? It’s easier than a direct compliment because direct compliments sometimes have the unnecessary pressure for the recipient to respond. I have nothing against complimenting a woman though. I just think indirect ones are a great way to start things off if you’re feeling gun shy.

It also tells her you think she’s attractive without making it seem like it’s the only reason you want to take her out (even though at this point that is true, women want to feel like you want to “get to know them better.” If she thinks you are only going out with her cuz she’s pretty, that’s when she’ll question if you are only interested in a physical relationship)

If you don’t want to chit chat further as you’re probably going to be super nervous, you can say…

“I’ve gotta run but can I call you sometime?” And then if she says yes, just take out your phone and say, “425 area code?” to get the ball rolling.

And as you leave tell her to have a great day and tell her you will call her:)

if she says no, the exit strategy is to smile and say, “Well, I’m sorry for interrupting you. Enjoy the rest of your day.”

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Article written by:

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.

Join the discussion

  1. hunter

    How about, “I like your shoes, did your husband get those for you?”……

  2. Phil

    Hi MidoriLei,

    I just realized the difference between how I initiate conversation with people I’m now friends or acquaintances and how I initiate conversation with women I would like to ask on a date: I rarely approach people directly to make friends. Instead I usually find myself in some situation that puts me in the same situation as another person and I start talking to them. That’s how I’ve become friends with all the people I’m friends with. As for attractive women, I usually have to approach them directly which is awkward enough for me since that’s not how I normally make friends. I don’t know what to make of this. What do you think?


  3. Anonymous

    I love it. Girls like me are sure to hit and get with a guy if he shows humility and confidence at the same time.

  4. MidoriLei

    hunter, hmmm… love it, but might she think you play for the other team? lol

  5. MidoriLei


    The way you make friends doesn’t necessarily have to mirror how you meet women. I can see how it is awkward to meet women as it’s not how we meet friends. The risk you take in looking like a fool by putting yourself out there will pay off if she says yes. If she says no, it will also pay off as you will get used to the feeling and will eventually be able to shrug off a no. Trust me, it gets easier, and for many men, the process actually is ENJOYABLE.

    You need practice in being confident approaching women. That’s all. My brother wrote this amazing article about confidence:

    The difference too with friends is that you are bound by common interests and the like… but with women…

    it’s all about eros and attraction, not just common interests. That’s why it’s appropriate to just go up to a stranger. Because you only need attraction/eros to compel you to approach a woman.

  6. hunter


    ….How funny, play for the other team?…..

  7. MidoriLei

    Hunter do u know what I mean? Sometimes when men notice style, a woman’s gaydar goes off… But only sometimes:)

  8. hunter

    … so??….

  9. MidoriLei

    Gay men tend to notice style and fashion more than straight men

  10. Johnd609

    I truly appreciate this post. I’ve been looking everywhere for this! Thank goodness I found it on Bing. You’ve made my day! Thank you again! dcceeeeedeae

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