In my last post, I talked about how technology has affected dating in modern times. No matter how much it has changed from the past, the fundamentals are still the same. The guy usually always makes the first move. Even when you get a match on Tinder or other dating apps, guys are expected to text first. Today I want to talk about approaching and making the first move. I think it would make sense starting from the beginning and go through the process of dating and relationships with every post. How to approach...well it's not rocket science so how hard can it be? It really depends on you. It will be difficult if you over think it and have doubts. However, if you confidently go up to a girl and naturally talk to them without thinking about it too much then it will be fun and easy. I myself at times have these moments where I don't approach and it's a missed opportunity. How I think about meeting girls is related to gambling as odd as that sounds (pun somewhat intended). If you think about it, there is no probability of winning any money if you don't risk betting; similar thing with approaching women; no risk, no reward.

Crawl Before You Run

Some people are more extroverted and some are more introverted, either way everyone has to start somewhere. If you are shy to begin than we will start with learning how to crawl before we start running. Before you even start speaking with someone, try getting some eye contact with someone no matter how brief it is, simple and easy, just to get comfortable with some type of interaction. It's also safe and with the least effort. Of course, it also has low results. From there you can also start having minor conversations with anyone when you go out. Whether it's a guy, a girl, old or young. Anyone! You're wondering why would you want to talk to a guy or someone you're not interested in and the reason is because there's less pressure and it's casual. Speak with the bartender, people near the bar, or the servers to get more confidence in initiating. These conversations don’t last long and are not meaningful. Ask how their night is going and make small talk. Main focus is getting you to initiate, because if you can’t speak to any random stranger, then there is a high probability that you will not make the first move to a girl you are enchanted by at first sight.

Importance of Location

For starters, go somewhere that interests you and that way you have some common ground to start a conversation. Events like festivals, concerts, art galleries or sporting events will give you a topic to talk about right off the bat compared to general places like bars, clubs or the mall. There is one location in Winnipeg, which is a good start to get some experience mingling with people is at Across the Board Game Cafe. They have singles night every month which they group men and women evenly in separate tables to play board games with each other. This is a better option, in my opinion, than going to a grocery store and tying a plastic bag to your cart or basket. There's a higher change that you will be talking with someone since you are exchanging seats, playing different games with different people in rotation.


I admit, I was not interested at all in going to this but our friend Richard (one of our bloggers...) suggested we go, since I jokingly said that speed dating would benefit him. However, the event focuses more on the board games and less on the interaction but it is entirely up to you to pay less attention to the game and more attention to the women around you. Even if it isn’t singles night, you can ask a random girl if they would like to play a game and go from there. I can’t imagine any other way this can be easier, unless the girl approaches you first!

Level Up With Experience

Once you are experienced enough with approaching, it will come second nature to you and you wouldn’t even second guess yourself before you take the first step. Just like with everything, practice makes perfect! In addition, the environment that you are in will not matter as you progress with approaching and you will adapt to any situation. Even if you get rejected, the fact that you made a bold move of going up to someone is a victory in itself. So don’t think of rejection as a loss, learn from it and know that you were confident to make a move. It is common to get rejected as well. Just like how it is with gambling, you win some you lose some. The only difference is you are gaining experience and insight with each loss. I know it is not a good feeling and your self-esteem gets a hit but soldier on and you'll end up with thicker skin that rejection will not affect you as much.Think of it as a win-win situation!
~Jay Alarcio