Ask Single Dating Diva: Should a Woman Make the First Move?

Traditionally, men pick up, or pull, women. Women can either accept or not. This is true online and offline. But what if the woman makes the first move? Should a woman make the first move? How does it make her look? Does it emasculate the man? Would it work in her favor? All good questions, all questions I’ve been getting a lot recently. What do I think? Should a woman make the first move? Here’s what I advised one reader …

Should-Woman-Make-First-MoveDear Single Dating Diva,

I’m an attractive, fit, successful single woman in her 30s. I’ve been single for a while and having difficulty meeting someone. Men don’t seem to want to approach me when I’m out in public. They stare and I smile at them and encourage them, but, inevitably they don’t approach. I’ve been hesitant to approach because I don’t want to seem aggressive or emasculate them. Do you think it’s OK if I approach them? Should a woman make the first move or would that paint her in a negative light and ruin her chances?


Woman on a Mission

Should a Woman Make the First Move

Dear Woman on a Mission,

Thank you for your email and question. I totally can see how it’s difficult to know what the right protocol is, especially since you’d be taking the “nontraditional” approach. Myself, I’m more of a traditionalist when it comes to dating because of personal preference, but I certainly don’t think it’s the only option. Sometimes you do have to take matters into your own hands and just go for it. I think there’s nothing wrong with it. However, I think your approach is important. Making a move, either online or offline, takes some tact and judgment when dating. How so, I will explain.

Should a Woman Make the First Move Online?

If you’re online dating, it’s completely fine for a woman to make the first move if you saw a profile that peaks your interest. Here are some tips:

  • Read the profile carefully to learn more about who they are and what they are looking for because you want to make sure you are a right fit for them.
  • If you want to be subtle, then send them a wink or flirt (or whatever the equivalent is on the site you’re using). See if they respond, if yes, great, if not and you’re still interested send a message.
  • If you don’t care about being subtle, then send a message directly. Make sure that it is friendly, brief and strategic. Just say “Hello [name], I’m [name] and I saw you’re profile and think we would be compatible. [explain in one or two lines what in their profile makes you compatible]. So if you are interested, check out my profile and drop me a line. It would be great to chat. Best of luck!” … simple, to the point and puts it out there by making it clear why they should speak with you.
  • If someone clicked on “favorite” or “like” on your profile then it’s an easy way of knowing that they are intrigued so check out their profile and send them a message.

Should a Woman Make the First Move Offline?

Making the first move offline is as simple as being friendly and just engaging in conversation with people. It doesn’t have to be scary or intimidating. Here are some tips:

  • When you’re out in public places doing your normal everyday activities, chat people up. It will give you practice talking to strangers.
  • If you see someone you like, just talk to them about something that’s completely NOT picking up. For example, if you’re at the coffee shop line together ask them what they’re ordering saying you can’t decide. If you’re at the grocery store, go to the section where they’re at and tell them about your favorite brand of what they’re picking up. When it’s done casually it doesn’t come across as aggressive.
  • When you’re out at a restaurant, lounge or bar something that works is the “5 Second Flirt“. Essentially, if you’re interested in someone, you look at them and smile for 5 seconds and then turn away and then look back. Your body language should be open and friendly. They should approach you. If not but they smiled back and encouraged you then go over and chat them up. You never know unless you try, right? Again, leave it in the spirit of friendliness and discuss your surroundings which makes it less threatening for both and easier to do.

So there you go … should a women make the first move? Why not! What’s important is that you act with dignity and grace, understanding that not every “conquest” will be successful. Take it all in a spirit of fun and don’t take things personally. You never know unless you try, right? Go forth and pick up my friends!!

READERS: Women – have you made the first move? Men – what do you think of women making the first move? Would love your insights and experience in the comments below!!

Your Sister in Dating Bliss,

Single Dating Diva

Copyright Single Dating Diva


  1. I made the first move with my shy, silent type. I said hi, asked his name. Eventually, I sat down next to him when I spotted him on a bench outside. Things were majorly awkward at first, but eventually he suggested lunch. Some men just like a little encouragement so they feel secure making moves 🙂


  2. I think it is time to throw out those old traditions out the window. Man or woman if you like someone go say hi you never know what will happen. Besides us men sometimes need a blinking light to know what is going on.


  3. I’ve come to the conclusion I have to make the first move. The guy I like is super shy. I figure the worst will be a rejection. I’ve had guys tell me they liked me but were shy and had I known this maybe things would have been different in my life instead of me being 44 and still single.


    • Thanks Dawn! You can’t really predict what could or could not have happened if you made a move … but what you can do is change how you act now. I think you should make the first move! Tell us what happens!


  4. From a 21 year old’s perspective: I always made the first move probably since I was 13 andddddd let’s just say it never ended well. When I was on POF a couple years ago (where I met my boyfriend and the best person ever) I did my fair share of sending out interest messages first, but I will say, he contacted me first and the rest is history 🙂 Now, I never thought women shouldn’t make the first move because some guys like a woman who knows what she wants. I think, tread with caution and do whatever is most comfortable for you: if you’re a more blunt and forward person, like myself, maybe drop the reins a tad and let someone pursue you and get to you.


    • Thanks Audrey! There is absolutely nothing wrong with sending an encouraging glance or saying hello. The secret to success is the approach. There’s certainly no right or wrong answer here but it never hurts to try!

      Liked by 1 person

  5. Thank you Diva for this. There’s nothing wrong with women making the first move. Nothing wrong at all. In fact, I even think it helps the relationship (if it develops into one).


  6. I’m old fashion, I allow the man to make the first move. its worked well for me both in person and on line dating as well. Tradition isn’t a bad thing. I have a teen age daughter, and her rules are guys chase girls and girls don’t chase guys. Men are hunters so allow him to chase you. But every parent is different .


  7. Oh boy… this opens up such a can of worms! Honestly, from my experience there really is no “one size fits all” answer. It depends on the person initiating, as well as the recipient, and layers upon layers of extenuating circumstances to boot! If it works, it works. That’s all that can really be said!! Haha! Know yourself, ladies… if you find that taking charge can be a weakness you’re trying to tame I wouldn’t advise doing so when trying to establish a new relationship! And, that’s only one of the many scenarios that may be at play here! It speaks nothing to gender roles or anything… personally I say gender roles have very little to do with how you should behave here!


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