Before I get to the story, we’ve all run into this situation before. How far is too far? Eastside, Westside, Uptown, Downtown, Brooklyn, Queens? For me, as long as I can get there by subway, it’s not too far. The PATH is usually a stretch for me, but I’ve been known to attempt a date out in New Jersey.

During my last family visit to Long Island, I stopped by my brother’s job to meet him for lunch. After my quick stop into the ladies room to primp, this guy walked out of the men’s room at the same time and smiled at me. Turns out, it was Little Dougie from the 5th Grade. Well, not so little anymore. I’m not sure what came over me but I ran over to him, gave him this huge hug and after some small talk, I told him to give me a call the next time he was coming into the city so that we could catch up. Thinking back, I find it amusing that I didn’t even consider telling him that this city girl would meet up on the Island for a drink. God FORBID!

Since that time, we’ve exchanged a few calls and made plans to meet up for a drink in the city. That’s when my male friends all chimed in to say that no guy is going to travel to NYC on weeknight from Long Island if he isn’t interested. Really??? As flattering as that might be, I’d actually like to think that some people ARE that adventurous and DO want to spend a night out in the city just because they can. Hmm. Now that I write that, it does seem a bit far-fetched. Thing is, I hadn’t really put much thought into Little Dougie as anything other than a fun blast from the past. Not for any particular reason, but the city girl / county boy thing certainly comes to mind and we have that geographically undesirable thing going on because he REALLY lives way out there. That didn’t stop me from flirting a little since he’s quite the cutie… but in my mind, it was entirely harmless because I’ll admit that I have a terrible habit of flirting for the sport of it.

All that aside, I look at it this way – any guy that’s going to travel THAT far during the week for a drink is worth learning more about.

He came in last night. Train arrived at 8:00pm and we settled in at Stout on 33rd Street since he had to take a 10:30pm train back. Not a lot of time, but enough to stroll down memory lane, catch up on the turns our lives have taken, and find out what Little Dougie had in mind. The boys were right. I wasn’t sure at first, since you can’t really tell if they’re flirting for the sport of it too, so when it got closer to 10pm, I had to ask. :) Guys get so flustered when I do that. I know, it’s a little mean but I figure it’s always better to know than to wonder – for both parties. Of course, the problem with asking that question is figuring out what YOU have in mind. After all, fair is fair.

Without going into the details, if Little Dougie (yes, I know I’ll have to stop calling him that at some point) asks me to hang out again, I’m saying yes. I can’t imagine being one of those women who completely avoids a potentially good catch just because he doesn’t live in NYC. However, there isn’t anything appealing about the LIRR. I guess some exploration is in order.