How To Approach Women With Confidence: Guest Post

The Mingle Master takes dating and picking up to a new, classier level.  His practical go to guide is a must for all men who are looking for something real.  Enjoy!

Approach-Women-With-ConfidenceApproaching women is hard. It takes guts. But, there are definitely some things you can do to make it easier. If you’re looking for a more lasting relationship rather than just a hookup, then here are a few tips for you.

I have two goals when it comes to approaching women with confidence:

  1. Keep my dignity if it doesn’t work
  2. Establish myself as a quality person if it does work

I have had female friends tell me that being approached by a stranger can be scary. Men often don’t realize this. A man who has any respect at all for women takes these fears into consideration when approaching a woman he doesn’t know.

Approach Women With Confidence: Five Stages

Stage 1: Have a casual mindset.

Approaching women is not a big deal. Don’t make it one. You should have a casual, just hanging out kind of attitude.

Stage 2: The ice breaker.

You need a reason to start a conversation. The ice breaker should be something reasonable. My all-time favorite ice breaker (even in non-dating situations) is “Are you from __________(fill in the city where you are located).” It should be easy to continue the conversation from there.

Here are some other ice breaker ideas:

  • The eaves drop. If you overhear a conversation sometimes you can smoothly make a comment and enter into the conversation. Just be willing to leave quickly if it looks like the people involved are annoyed.
  • The opinion request. One thing I love to do is to ask strangers about their favorite restaurant when I’m out. Sometimes they may tell you quickly and leave, other times they may start a conversation. Either way, you have approached and given yourself a chance. Feel free to use other opinion topics, just make sure they don’t sound forced.
  • The proximity attempt. Do your best to get close enough to make a throwaway comment to a woman. This goes for anywhere you may find yourself–the grocery store, coffee shop, bookstore, whatever. Don’t be a creep about it, but if you can find a way to be hanging out nearby then you can approach in a much friendlier and less intimidating way.
  • The light compliment. Compliment something from her outfit or something that stands out. Unless your only objective is just to try to sleep with her, do NOT start out by saying something about how cute, beautiful, hot, etc. she is. This sets up the focus of your interactions to be about her looks. You never, ever, never want to start a relationship as a kiss-up or superficial person.
  • The elevator play. If there is a situation where you have no time to chat, then the direct approach may be your only choice. If this happens, go straight to the “Are you from_______” question” and then ask if she’s single. This approach is a little dramatic and it should only be used as your last option.
  • Say “how are you” like you know the person. See what happens.

Stage 3: The Conversation.

This can take a few minutes or a few hours. Doesn’t matter.

Stage 4: The vibe read.

I don’t care how good your game is, there are going to be some women that you just do not click with. Assessing the connection should be a top priority.

Stage 5: Getting contact info.

If there is a good connection then it’s time to try to get her number. A good transition to get you to this point is to say something like “You aren’t single, are you?” If she is, ask for a way to get in touch with her. The more casual, the better. At this point, she has shown herself to be interesting enough for you to want to see her again. This is a much better place to come from to begin a possible relationship than starting right off with trying to date her because you loved her looks.

The Mingle Master is a teacher of the arts of socials skills and dating. Check out his blog and follow him on Twitter!

Your Sister in Dating Bliss,

Single Dating Diva

Copyright Single Dating Diva


  1. Great tips here – Thanks……. I’m really tired of trying to find that “more lasting relationship ” on those silly and useless dating websites. The biggest problem I have is getting past the chatting stage and moving forward. Thoughts come up like “no ring on her finger, but is she single?” or “is she just being friendly”. Anyway, guess I just have to put myselve out there more – Nothing ventured, nothing gained.


    • Dan–Glad you liked the post. Getting past the chatting stage is a common problem. You aren’t alone. If she has no ring, feel free to ask if she is single. It’s okay if you find out she isn’t. Don’t feel like you have to read her mind. Just ask casually and be prepared to go for the contact info if she is. Sometimes you get it, sometimes you don’t. No big deal. Good luck!


      • Thanks……I have of late been more proactive in talking with ladies and moving in that direction, as you say. I do know that not many ladies (none) will put themselves out to get to know who I am and ask. Of course asking about if they are single, will for sure send a clear message on what my intentions are. But as you know, nothing ventured, nothing gained. I have had no luck at all on the two free dating sites – Plenty Of Fish and OKcupid. So I figure, what do I have to lose chatting with strange women and possibly finding that elusive ” lasting relationship “


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