Getting the Courage to ask a Woman Out

So you like someone … or you see a girl you like from across the room.  What to do? If your first instinct is usually to run, then no wonder you’re single.  It’s the assertive guys who get the girl … don’t kid yourself.  Although it may be a nice idea, a woman isn’t just going to fall into your lap … you’ve got to go get her!! In my experience I get a lot of “sir stares a lot” and not enough “sir asks me out”.  What ever happened to guy sees girl, guy APPROACHES girl, guy asks girl out and guy and girl go on a date? It’s just not that easy anymore, is it?  Getting the courage to ask a woman out could be the scariest thing you do but can reap lots of reward! It’s simple really … it is! So, here’s what to do!

Getting the Courage to ask a Woman Out

The Approach

53% of singles find a great smile the most attractive feature in someone. [/quote] You see a woman you like.  She may be on the street, in the store, at the bar or even at work.  Just look at her, check out her body language.  Does she seem closed off? Does she look at you? If she looks at you – smile.  Does she smile back? If she does, that’s a green light to just approach her.  It doesn’t mean she’ll say yes, but at least she’ll be open to saying hello.  In fact, 53% of singles find a great smile the most attractive feature, most likely by smiling at you she’s making an effort to be attractive to you.

If she gives you a dirty look or doesn’t give you any positive body language, then don’t bother.  But, if you have the green light to go say hello, do it!  Take a deep breath and walk over.  What’s the worst that could happen? She says she’s busy and can’t talk.  That’s OK, at least it wasn’t a missed opportunity.  You don’t know unless you try.  So walk over … approach her.  Just start by saying “hello, I’m [insert your name]”.

No Pick Up Lines PLEASE

No one likes a pick up line.  No, really, they don’t work.  They are cheesy and irrelevant.  Woman are much smarter than that and the only thing a pick up line will do is get you rejected or laughed at.  So don’t do it.  There are much more intelligent, effective and useful ways to speak to a woman that will make you more likely to get that date.  So put the rule book away and burn those pick up lines!  Here’s what to do.

Flattery Will Get You EVERYWHERE

Who doesn’t like getting a compliment?  Really?!  Everyone likes hearing they look attractive, or what they are wearing is nice.  Women particularly like this.  I don’t care how humble they act, they love a good compliment from a man.  I know I do … sometimes if they cater too much to my ego I do drop some of the bricks off my wall.  I know, shameful isn’t it, but it’s my big Leo ego.

1% percent of single people surveyed say that flattery is the best way to attract someone. [/quote] I read that 51% percent of single people surveyed say that flattery is the best way to attract someone.  So there you go, what was it that attracted you to her in the first place?  Her hair? Her smile? Her face? What she’s wearing? The way she dances? So, tell her.  Just don’t be creepy or sleezy about it.  Stay classy and normal.  Just say “I noticed your [insert what you liked] and wanted to let you know I really liked it”.  Recently, a guy loved my red hair and it drove him crazy, he kept telling me so, I melted … more about that story another time.

Common Interests

People usually date those of common interests.  That’s really a no brainer.  People want to be around others who are like them and like to do the same things.  Chances are you have something in common because you are in the same vicinity.  You need to use this opportunity and whatever it is you’re both doing to continue your discussion.

Let’s say you’re at a store.  You are both in this store.  This is a common interest, even if it’s a grocery store.  Talk about the store, talk about why you like the store, talk about something interesting that’s happened to you there.  For example, you could say “I come here often, I really like their selection of international foods”.  This could open up a whole new discussion topic. (PS: if she’s buying condoms no you can’t use that as your reason to approach)

Ask For the Date

Once it’s the right time to take the next step, it will feel comfortable and natural.  So just do it.  Take what she said about your common interests and ask her on a date.  Keep it simple and casual.  For example, if she said she likes gelato, ask her to go for gelato at this great place you know.  If she said she likes nature, ask her to go for a nature walk.  If she said she loves gourmet coffees, go somewhere trendy for coffee.  Get what I mean?  Adjust the date to your discussion.  It makes it a natural progression and you’re more likely to get a yes.

Does It Work?

Well, these things definitely work for me and most girls I know.  If a guy has enough balls to approach me then I respect that.  I don’t smile at anyone that I wouldn’t be interested in talking to.  When I do smile it’s a GREEN LIGHT.  No, seriously, come over and say hi.  I am so tired of guys staring and not doing anything about it.  For goodness sake I’m not a museum piece nor is any other woman!! Just do it!!!

To Recap = smile, if she smiles back approach, introduce yourself, compliment/flatter her, tell her why you were attracted to her, talk about common interests, ask her out on a date that caters to your common interest … enjoy!

Your Sister in Dating Bliss,

Single Dating Diva

Copyright Single Dating Diva

Originally Published on Singles Warehouse


  1. Although I am a pretty shy introverted guy, it has never been so much getting the courage to ask someone out, as I generally just assume I am going to fail at it, in which case I either get the expected result (no), or a better than expected result (yes). That was always the easy solution for me.

    The real problem is actually meeting people whom I would want to ask out. With people I just met (or worse saw) randomly it is really hard to gather enough information about them (without turning into a creepy stalker!) to determine if have anything in common. at all. All you have to go on is looks which isn’t nearly enough.

    If I think about how many online profiles I click on, based on the picture and perhaps age as that is what is on the list, there is probably less than half of the profile where I can even find enough of a topic to mention something more than “hi” in an e-mail. Needless to say, no e-mail gets sent and I click onwards down the list.

    There are a few things you can sometimes visually spot. Seeing someone commute each day generally means they are employed. Do they carry a lunch? Good they are perhaps sensible with money. Sometimes they carry a few props that might point to an interest (ie a squash racket), but not all women carry their hobbies around with them I generally have to see them a number of times to infer much. Otherwise they just get relegated to being the hot women on the bus in the morning…or whatever. The only real hopes are co-workers (terrible if in a gender dominated field) or friends of friends.

    I also generally like to figure out if the person is in fact single if I possibly can. That usually entails talking for a bit which is not always easy or even possible.

    I don’t want to just see some women and go on looks. That’s awful.


    • Thanks for your comment John. It is hard just to meet someone compatible you’re correct, however, you never know unless you try. So, in your opinion, just attraction isn’t enough to make the move?


      • No, I certainly wouldn’t approach someone on looks alone. Doing that would be something for a one-night stand, not someone I want to keep around. For long term you can’t count on looks. You need other character traits that will last a lifetime. This doesn’t mean looks have zero value, but average is fine and probably lower maintenance as bonus.


      • [Hopefully this orders right, this doesn’t seem to want to nest more than two levels – reply to October 11, 2012 at 6:14 PM]

        Attractive women certainly have good qualities! And not just looks! It is more that, just by looking, a guy wouldn’t know of these.

        The other issue with attractive women is that because she is so attractive she has tons more choice of guys and that considerably lowers the guy’s changes. Comparing again with online dating, there is many profiles I look at where she is clearly looks amazing and her profile looks good too, but I then I think that her mailbox must be completely overwhelming and there is therefore little chance of a reply to a cold message. I usually decide that I will leave it to her to send the first message if she is interesting. Sending the first one is a waste of time as she won’t have time to read it.


  2. This is a great column – with really helpful advice. For me however, I usually assume that a woman who interests me won’t feel the same way about me. Although I do smile, As you suggest, I don’t approach because I always find myself thinking she could do so much better than me. I have several female friends, many of whom are very attractive, and even though they wonder at times about I’m not dating anyone, I can’t seem to stop feeling that I’m not good enough.


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