Flirting 101: Train spotting [part 2]

As I continued to steal glances at hipster boy, noting the adorable way his blue plaid shirt perfectly matched his sneakers and his skinny jeans straddled that line between too tight and just tight enough, I felt compelled to let him know how attractive I found him.  I liked his style, but more importantly, he was just darn cute.

I spent the majority of the train ride debating whether or not the chance at conversation with hipster boy would outweigh the fear of talking to a complete stranger.  The Match project has certainly made me more comfortable with conversing with someone I've never met, but I still rarely start an interaction that's not warranted by someone talking to me first.  However, when hipster boy moved from standing near me to occupying the newly emptied seat directly next to me, I felt obligated to seize the opportunity.

Frankly, it would not be completely unheard of for me to go the crazy stranger route and simply turn to a boy and say "You're really cute" out of nowhere. Thankfully, on this particular occasion, I found a conversational in. You see, hipster boy was wearing headphones.  Not earbuds, but old school, DJ spinning headphones.  You can find them often at Urban Outfitters which almost definitively makes them a hipster trademark.  I've noticed them often around the city and always wondered if they were functionally superior or simply stylistically cooler than my measly little buds.  Emboldened by my non-crazy reason to speak, I tapped hipster boy on the shoulder.

Me: "Can I ask you a question?"

Hipster Boy: "Shoot." [his casual and still friendly response made me like him even more]

Me: "Are those type of headphones better than earbuds? Like do they have a better sound? Or is it simply a style choice?"

Hipster Boy: "Well I like them because I think they're more comfortable. I don't like sticking things in my ears. But they also have a better sound. You can hear the bass clearer.  Your ears aren't being bombarded by the sound the way they are with earbuds." [boys who know music are sexy]

Me: "Ok, I always wondered if it was just a style choice or a musical choice."

Hipster Boy: "Yeah, I just like them better all around."

Me: "Ok...You're hot by the way."

Hipster Boy: [flattered and only mildly scared by my craziness] "Well thank you."

Me: "I figure it's always good to hear that."

Hipster Boy: "Yes, yes it is."

And that was the end.

We went back to our respective iPod music [mine connected to earbuds, his to the musically superior headphones] and a few stops later he exited the train.  Best part: I didn't feel rejected at all.  I'm glad that I spoke to him.  If I'd let him sit in silence next to me for the entire commute, I would have always wondered what might have happened if I'd just said what I was thinking.  Following my gut instinct felt good.  Plus, it opened a window of opportunity for him to return an interest.  So what if he didn't take it? At least he went home that day feeling a little bit hotter.