I went for another run yesterday. On the way out of my building I saw the light on in the exercise room and I decided to see who was there. I secretly wished this really hot neighbor of mine were there. Her name’s Eve and she’s one of those really hot and sexy single moms but in a very down-to-earth kind of way. We talked a few times months ago when we happened to be in the exercise room at the same time but I didn’t pursue it any further by asking for her number – dumb mistake on my part. Did I mention she’s very sexy, too? Normally I would just pass by and not look in since I was planning on running outside. But today, I thought, hey, why not, let’s see who’s there. Alas, it turns out Eve wasn’t there but an elderly woman from my building who was on the treadmill and watching some mindless TV. We ended up chatting for a bit and I’m feeling pretty friendly and open about the run ahead of me. Feeling the good karma.

This is kind of a long post so if you just want to get to the pickup up part, you can skip to the last paragraph.

As I start my run, I pass by the Starbucks coffee shop that the other day I didn’t have the guts to come into after my run so I could talk to some random woman there. This time, though, I make sure to look inside so I can at least scope out if it’s worth coming into on the way back. Lo and behold, I see my good friend Kevin there! That was a serendipitous coincidence since he was just over at my place the other week and he wanted to invite me over to meet his wife. So now I definitely have a good excuse to come inside and so I do – with all my running gear. We end up chatting for a few minutes and as I’m saying good-bye to Kevin and get ready to leave, a woman calls out my name (Dating Guy! Dating Guy! Just kidding…) Turns out a friend of my sister’s is there whom I’ve known for many years (but am not interested in). So I go up to her and we end up talking for a few minutes. Now I’m feeling like I can move around this coffee shop as if I’m at my own party where I know everyone. When I say good-bye to her and start walking towards the door, who do I see but Eve! This is quite serendipitous and I can’t believe my luck. One problem, though – she’s sitting with this guy and I’m guessing they’re out on a date. But it’s a coffee date and they don’t seem to be touching each other a lot so I’m guessing it’s probably a first date. Still, I was just thinking about her minutes before and to have her be right there, well I can’t let that opportunity slip away. So I go up and say hi to both of them. I can see that I might have interrupted a private moment between the two of them and I don’t want to seem like some jerk who’s stealing away Eve from this guy. At the same time, I can tell she’s happy to see me and it’s good to reconnect with her after all these months. We catch up for a few minutes and then I excuse myself and let these potential lovebirds get back to their date – after all, I still have my entire run ahead of me.

So I go off on my run. I run through the path in the park just enjoying being outside. The weather, though, is not co-operating and it’s starting to rain and the wind is picking up – this didn’t bode well for finding attractive women just out and about. I didn’t let that deter me and continue running, still managing to say hi to virtually everyone I pass on my way. About halfway through the run I ran into the same 92 year old man I met on my last run – and at almost at the exact same spot! Man, that’s a lot of coincidences for a single day so maybe I had good karma today. We greet each other like two long lost friends and talk a bit more this time. He tells me how he has a 107 year old friend that still drives and is in excellent health who runs regularly and I ask him more about his longevity habits (amazing how the quest to learn to pick up and meeting more women has these side effects of learning how to live a longer life). He even asks me if I have a girlfriend and I tell him that I don’t and wonder if this 92 year old is hinting that he wants to set me up, but he doesn’t pursue it. Then he asks me if I’ve told anyone about our meeting and I tell him “yes, indeed I have, to many of my friends” which isn’t a lie because some of my friends do read this blog. Um, I didn’t really want to tell him that I’ve shared our meeting with all my blog readers. Then again, he might not have cared.

I continue my run for home and this time I’m determined to stop in at the Starbucks on the way back – what I couldn’t do last time. Besides, I’m curious if Eve is still there. So I get closer and closer to the coffee shop and my curiosity is building and building. I don’t feel as nervous as I did last time. Maybe it’s all the good interactions I’ve had with people already and it’s no big deal to come into a public place – even though I’m not going to buy anything and even though I’m dressed in my running gear and even though I’m going there to socialize with women.

I manage to blow my nose and make myself as presentable as can be expected before I’m in view of the patrons inside the shop. I start running by the store window and Eve is still there! But so is the guy 😦 Well, now I’m coming in for sure so I do and I reconnect with the two of them. We end up talking longer this time since I’m already done my run and I make sure to include the guy in our conversation even though it’s Eve that I’m most interested in. I tell them I don’t mean to interrupt their conversation and the guy tells me “that’s OK, I’ve been talking mostly”. I thought that was kind of a strange thing to say – he’s been talking mostly? Why not let this glorious woman talk and express herself, as I’m sure she yearns to do. So I ask her more about the stuff she’s been up to. I really want to ask her deeper questions… questions where we can really connect with each other. But I’d feel kinda weird doing that with Mr. Talk-Too-Much sitting right there. Maybe he thought I was encroaching on his turf? I made sure to include him in our conversation, but I must admit my eyes wandered more and more towards Eve. Man, she’s a fine looking woman! After a few minutes of us chit chatting I excuse myself – I should’ve asked for her phone number but to do it in front of Mr. Talk-Too-Much would have been weird. Maybe I should’ve asked her what suite she lives in so I could just knock on her door to “borrow some sugar” one day. But I didn’t – I just said bye to both of them.

So after I’m done with Eve and Mr. Talk-Too-Much, I look around the coffee shop. It’s pretty packed with people and I’m looking around for any single looking females. I spot two women sitting by themselves with books out – obviously studying, and yet, they seem to be talking amongst themselves. As I mentioned in a previous post, my theory is that women who study at coffee shops want to be distracted or maybe even romanced. One of the girls is the “cute one” the other is the “ugly friend”. So I come up to these two and just say something like “Hi, I just came in here to rest up for a bit and I was wondering if I can hang out with you guys?” Now, remember, I’m in my running gear and it’s been raining outside so I’m pretty wet. They first look at me a little startled but I can see that the Cute One might be open to talking further. The Ugly Friend is giving me a bit of the evil eye. I’m actually feeling pretty relaxed because I just don’t care at this point. I’m just happy that I’m doing this – something that I couldn’t do just a couple of days ago. The Cute One says something about them having to study for exams. I ask the Cute One more about the exam and when is it and she says that it’s next Monday and I joke that she has plenty of time to hang out and take it easy. I ask the Ugly Friend what she’s studying and she says Human Resources, but in a not so friendly way. I couldn’t understand the Ugly Friend’s resistance – maybe she was having a bad day but I could sense that she wasn’t amused by my attempt to make friends with them. Who knows, maybe she’s jealous of her cute friend for attracting attention, I don’t know, and I wasn’t about to start psycho analyzing her. So after a bit of more small talk I leave them to “study” (yeah, right). As I’m about to head off, the Cute One says she’s really sorry that they have to study and my intuition tells me that if I had caught her by herself she would have been more open to the interaction. I just reply “Please, don’t be” as in “Please, don’t feel sorry for me, lady, you just missed your chance to have a fun evening – your loss”. And with that I exit the coffee shop and walk the rest of the way home. I break out into spontaneous bursts of laughter as I’m walking home in the pouring rain. Everyone else is inside, or under umbrellas trying to quickly get to where they need to go. Me, I’m just laughing and taking my sweet time getting home – I did it! I overcame a personal fear of mine today and it wasn’t even that big of a deal.