I don't believe there's an ideal occasion or opportunity to meet new men and women. I used to make excuses like "It doesn't feel right," or "I have nothing to say!" to validate my nervousness and hesitancy. With experience, however, I recognized that the perfect time and best way to approach a woman is when you just swallow your pride and shoot your shot.
Since people are everywhere, there are a limitless number of places to meet women.
Here are places I've had luck:
Public transportation (buses, trains, taxis).
Social events and hobbies (concerts, dances, classes, parties).
Bars and clubs.
Online (dating sites, meetup.com groups, social media).
At school (college is an amazing place to meet people!).
Now before you mosey on up to the woman at the coffee shop, you should understand the concept of risk vs. reward and its effect 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.” (Investopedia)
With respect to dating: generally, being upfront with your goals (high risk) will enhance your potential progress with a lady. If you stick to casual conversation (low risk), she'll likely be responsive and welcoming 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 being denied, you're not taking enough chances.
Ready to talk to her? To make it easier, I've categorized three main ways to start a conversation:
Indirect-- Asking a pleasant question or for her opinion (low risk, low reward).
" Do you know where the nearest Dunkin Donuts is?".
" What are you taking pictures of?".
" How did you like the band?".
" I need some advice on getting my 5-year old neice a Christmas present. Any suggestions?".
Situational-- Commenting on something in the moment (medium risk, medium reward).
" Your dog is awesome! Can I pet him or her?".
" 5 bucks says this guy won't catch the train doors before they close.".
" This drunk guy behind me keeps bumping into me ... help !".
Direct-- Stating your intentions upfront (high risk, high reward).
" I'm sure this is gonna seem totally random, but I think you're cute and want to introduce myself. I'm Steve".
" 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 basic "Hi" (my fave).
All 3 ways to start conversation have their own benefits and problems. Some may work best depending on your character or the personality of the woman you're speaking with. Try using all three multiple times-- you'll start seeing what's more fun and works for you.
Don't be afraid to experiment and evolve. I find being direct or dropping a witty situational joke is best for me. Whatever you choose, try to look confident and always be genuine with your words. Ask a friend or a wingman to go out with you and have a good time because that's what dating should be about ... fun.
Learn to appreciate the experience and all that comes with it, because that's how you'll meet women.