Okay I am 19 and I'll start with a quick scenario. You're walking down the street and you see an HB coming your way!! You think "I got this!" But then you look slightly to the left/right and notice she is with her mom/dad.

How the hell do you approach that!?

In my case, I ran into this girl on tinder. We are both way into wakeboarding and she has met my sister a few times. We know a lot of the same people in the wakeboarding community but have never run into each other. We had a date planned but she had to bail for some reason. I didn't push another date after that. This weekend is the boat convention and they have an indoor wakeboard rail set up and she's good enough that they asked her to ride for the show. I went to the show and i was in the (small) crowd waiting for the event to start. When she got up on the deck she waved to me and smiled and i did the same. She rode and ended up wrecking. After I was looking for her to tell her good job and make sure she was alright but then saw her with a big group of people. All of these people i'd never met before but I noticed her mom was also in the group. I didn't dare approach! So i stood back a ways and waited on my phone for an opportunity but after about 10 minutes they all left together. I didn't know what to do and I just dont have the confidence to walk up and introduce myself. I know one of my mistakes was that i didn't bring a wing man. I would have felt a lot more comfortable if i had someone to fall back on instead of alone in this big convention.

So I'd like to know everyones opinion on this situation. Am I just being a pussy or was I too eager?

Thanks for reading this. I appreciate any input on this.

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Um...

It's one thing if she's with her dad, but if she's with her mom then things can be easier.

Win the mom over with charm and politeness and she will become your wingwoman. I've had moms give me their daughter's phone numbers right in front of them just because I said, "I'm just trying to get your daughter's phone number" after talking to them for a little.

And everyone says that confidence is so important, but functionally it's not. You don't need confidence to approach. You just need what we call outcome independence (in English that means "don't give a fuck what happens"). Confidence comes after you get a lot of experience and that confidence makes things a little easier. For now don't worry about it.

Also, bringing a wingman is oftentimes a VERY BIG MISTAKE. The fact that you think not bringing a wingman as a mistake is ridiculous but understandable. Common newbie misconception. Using a wingman when you have no confidence actually makes you look less confident and its a turn-off. Don't use crutches, put yourself out there, hope for the best, and let the mud roll off you with a smile on your face if anything bad happens.

Thanks for the reply man! I really agree with the approaching even her mom is around!

I do agree with not bringing a wingman other than I feel it might make me look like i don't have any friends and therefor might be a weirdo. Same reason the guy in high school that gets lots of girls continues to get lots of girls. Because girls are more comfortable with a guy who obviously knows how to be around girls.

But on the other hand, it also makes you look good because like you said, it shows that you have the I don't give a fuck personality which i personally think is attractive and i think girls think its attractive too. In his case, its like i'm there because i fucking like boats. Not to see her or to hang out with friends. And i don't give a fuck what happens because in the end i'm happy to be with my boats! hahaha

Well I'll be there tomorrow and ill approach unless she's literally in a position that i can't! Like if she is wake boarding all day and i'd have to jump in the water to say hey. haha I'll post back on how it goes!

Again, thanks for the reply.

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Um...

i totally agree, dad's can be a bit of dicks... mothers too but you have a better chance.

me personally i dont approach when girls are with their family unless i qualify, asking how they know each other and shes all like "yeah, this is my daughter. shes your age." HAHA

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When it comes to mothers and other older women, flattery gets you everywhere.

Act surprised when you find out she's the mother and say something along the lines of "you're not sisters?"

I never lie to the women I'm seducing but when it comes to potential "obstacles," I allow myself a pretty big grey area.