How To Meet Women
And Start Conversations

I don’t believe there’s a perfect time or opportunity to meet new people. I used to make excuses like “It doesn’t feel right,” or “I have nothing to say!” to justify my nervousness and hesitation.

With experience, however, I realized that the perfect time and best way to approach a girl is when you just man up and go for it.

Since people are everywhere, there are an unlimited number of places to meet women.

Some places I’ve had luck meeting women…

  • Supermarkets
  • Coffee shops
  • Book stores
  • Clothing stores
  • Malls
  • Gyms
  • Public parks
  • Public transportation (buses, trains, taxis)
  • Social events and hobbies (concerts, dances, classes, parties)
  • Bars and clubs
  • Online (dating sites, groups, social media)
  • At school (college is an amazing place to meet people!)

Understanding Risk vs Reward

Now before you run up to the chick at the bookstore, you should understand the concept of risk vs reward and its impact on meeting women. In finances, it is defined as:

“The principle that potential return rises with an increase in risk. Low levels of uncertainty (low risk) are associated with low potential returns, whereas high levels of uncertainty (high risk) are associated with high potential returns. According to the risk-return tradeoff, invested money can render higher profits only if it is subject to the possibility of being lost.”


In relation to dating: generally, being upfront with your intentions (high risk) will increase your potential progress with a woman.

If you stick with small talk (low risk), she’ll most likely be receptive and friendly towards you, but it’ll take more effort to hold her romantic interest.

Sometimes you’ve got to go all-in to see if she feels the same way about you; if you’re not getting rejected, you’re not taking enough chances.

Ready to talk to her?

3 Ways To Start A Conversation

Indirect – Asking a friendly question or opinion (low risk, low reward)

  • “Do you know where the nearest Dunkin Donuts is?”
  • “What are you taking pictures of?”
  • “How’d you like the band?”
  • “I need some advice on getting my 5-year old nephew a birthday present. Any suggestions?”

Situational – Commenting on something in the moment (medium risk, medium reward)

  • “Your dog is awesome! Can I pet him?”
  • “5 bucks says he won’t make the train doors before they close.”
  • “This drunk guy behind me keeps bumping into me…save me!”

Direct – Stating your intentions upfront (high risk, high reward)

  • “I know this is going to seem completely random, but I thought you were cute and wanted to introduce myself. I’m Nick”
  • “I have to tell you, you guys look like you’re having the most fun here!”
  • “Hey, you looked interesting and I wanted to come say hi.” or just a simple “Hi” (my favorite)

All three ways to start conversation have their own advantages and disadvantages. Some may work better depending on your personality or the personality of the girl you’re talking to.

Try using all three many times — you’ll start to see what’s more fun and works for you.

Don’t be afraid to experiment and evolve. I find being direct or making a witty situational joke is best for me.

Whatever you choose, try to look confident and always be genuine with your words. Get a friend or a wingman to go out with you and have a good time because that’s what dating should be about…fun.

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