The Cougar

I went to a friend's housewarming party a little ways back. Being that I had some vegetarian friends going, I took a shot at a vegetarian meatloaf. It came out amazing as it turns out, and particularly wooed the palette of a particular party-goer. She had to leave early, so we only spoke briefly, but apparently I made quite an impression on her. She contacted the host for my email address, and asked me out. Once again, how often do women ask men out? Seriously, twice in a month? Granted one of them was on a dating website where its more expected, but you have to understand I'm a bit old-fashioned, and was never really a ladies man. I think thats more times than I ever was asked out in my whole life. Maybe I'm just better looking now? Who knows.

Anyway I was not about to pass up an opportunity like this, so of course I said yes. She emailed back a bit, and I quickly took note how overly affectionate she was in her emails. Things like "hey handsome" and stuff that would be endearing had we met for more than a brief conversation about meatless meatloaf at a party. I didn't pay much attention to it, though, as I put more vest into meeting people in person. Then she bailed! We were supposed to meet on a Monday for lunch, but she never confirmed. I called the day of, no answer!

So I was bummed, but didn't take it too personally. She emailed me a few days later, guess it was just a bit of mis communication. So we rescheduled, then she canceled again. By this point I was tired of dressing up for work to just keep getting canceled on, but I gave her another re-schedule.

We finally met up for lunch at a sushi place downtown, and what a cougar! Now granted we had met, but you have to remember, it was really brief and quick. I don't think our age difference was apparent to both of us at the party, but she had to be at least 12 years older than me! I think over lunch I realized it more than she did. I look a bit older for my age, but there was an awkward moment when I mentioned "our generation". Unfortunately, I didn't find her that attractive, so I couldn't sugar-mom her up for show tickets and fancy evenings on the town. Maybe my next cougar.....

This is the kind of thing I expected to happen when dating without precondition. Not quite as dramatic as I expected, but still a good one for the books.

The Heavyweight

I got a message on a dating website asking me to go for a beer. It wasn't after a conversation or anything, just a straight up invitation to a stranger. That takes some serious balls, and I figured, how often do women ask men out? So in the spirit of no-precondition, I met up with her at a bar downtown. After viewing her profile I pretty much knew she wasn't was I was looking for, but I did it anyway. It may sounds terrible, but she was kind of a big girl and I wasn't physically attracted to her. Now I fully believe that some people become more attractive as you get to know them, but personality wise there were some clear indicators that wouldn't be the case.

But I met up with her regardless, and going in knowing it didn't mean anything made it really easy to be relaxed and enjoy myself. I think I need to just not be interested in people at all from now on. We ended up hanging out for like four hours just chatting about this and that. I still wasn't attracted to her, but her personality is similar to many people I knew in college, so getting along with her was easy for me. I do feel torn about the situation though, I kind of feel like I was leading her along. I'd like to stick her in the friend zone but that seems mean. I mean, I'm the guy who's usually really good at sticking himself in the friend zone, but never when I want to. I since haven't really spoken to her, online or not, maybe I'm a jerk.

Ketchups and The Forgotten

So I've been terrible at updating this thing, sorry. No excuses.
Anyway I'm going to make a few posts with relative updates in the single in philly world.

The Forgotten
I met up with an old friend over Thanksgiving, actually an old friend of my sisters, who has since moved away but we always had a thing for eachother. We ended up flirting a bit, things came out over drinks, etc, but I didn't pursue it at all. I'd like to think that I was being reasonable, considerate, sacrificing, and chivilrous, but maybe I was just afraid of being hurt. I can't help but wonder what I would have regretted more. Maybe I need to stop being so sincere. Perhaps it's easier to be nice than passionate. Either way I think I have a serious fear of being heartbroken again, and thats something I need to workout before I'm able to seriously date someone. Going on a stranger date isn't a big deal, we don't know eachother and its fun, but with her it would have meant something, and that was a bit scary.

Another First

So last night I went on a date with a friend's co-worker. We went out to a local Belgium place for dinner, followed by a nice bakery for dessert (quickly becoming a favorite of mine). Overall I think the evening went okay, but not great. I mean we get along well, but there were occasional awkward moments where neither of us had much to say, or we ran out of small talk ideas.

I think what really bothered me a bit was that I wasn't having a great time. I wasn't bored per say, but I also wasn't enjoying myself entirely. She was nice, but it seemed like we would have had a great time if we knew each other better. I like the idea of dating, but I think I need to figure out how to enjoy the dates themselves. Last night I kind of felt like there was a luminous cloud hanging over us, dooming our evening as a "date" with all of its associated expectations and titles. It reminded me a lot of the last date I went on (not surprise blind date girl), where it just seems to fizzle.

I'm not sure if such a thing means we just don't get along, or I just don't know how to enjoy a one-on-one evening well with someone other than my close friends.

I'm feeling a little unsure about this whole thing right now. For instance, am I expecting too much of a good time from a first date? Perhaps I have too high hopes for how I want my next relationship to start. Or maybe I just need to flex the dating muscles some more? I don't want to get discouraged and give this whole experiment up, but I need some kind of motivation to go on the next date. Hmmm....

So I need your advice, oh lovely audience: How do you make a good first date? I guess I feel like friendly conversation can only go so far. Perhaps finding a dating activity that goes beyond dinner+conversation? Give us something distracting?

Spooky Quizes

I took an online quiz on www.okcupid.com, which seems to ask a lot of personal information. Anywho, here are the results. Whats really funny is I think I actually look a bit like the picture! I even have a green shirt lol.

The Boy Next Door Random Gentle Love Dreamer (RGLD) Kind, yearning, playful, you are The Boy Next Door. You're looking for real Love, a lot like girls do. It might not be manly, but it's sweet. We think the next three years will be very exciting and fruitful ones for you. Your spontaneous, creative side makes you a charming date, and we think you have a horny side just waiting to shine. Or glisten, rather. You enter new relationships unusually hopeful, and the first moments are especially glorious. If you've had some things not work out before, so what. On paper, most girls would name the Boy Next Door as their ideal mate. In the real world, however, you're often passed over for more dangerous or masculine men. You're the typical "nice guy:" without just a touch of cockiness, you're doomed with girls. A shoulder to cry on? Okay, sure. But never a penis to hold. More than any other type, Boys Next Door evolve as they get older. As we said, many find true love, but some fail miserably in the search. These tarnished few grow up to be The Men Next Door, who are creepy as hell, offering backrubs to kids and what not. Your exact male opposite: The 5-Night Stand Deliberate Brutal Sex Master Always avoid: The Nymph (DBSD) Consider: The Maid of Honor (DGLM), The Peach (RGLM)

Expectations

So, I've had my first "date", which turned out almost as terrible as I expected, though not quite interesting enough to be a really funny story. I met up with "Girl B" from my craigslist post, but as I had mentioned, her post was more about meeting new people and learning the city than going on a date. Our communication via email was similar, seeming more like she was interested in just casually meeting people than actually dating. We decided to meet up at a local coffee shop she heard about for some sweet snacking.

Now, let me disclaim myself by saying that initially, as evidence from my previous post, I was looking for a date, but her carefree vocabulary regarding our meetup suggested she was not. But I decided to meet with her regardless to give it a try. After some poor service and awkward conversation, I realized it was a date after all, mostly cause I got stuck with the bill. Now, I consider myself a classical-modern man, meaning I like buying women dinner but not because I feel like I'm expected to. What bothered me about the situation was that we both clearly had different expectations. One of my friends pointed out that I did contact her on a personal's site, so I suppose I'm just as much to blame, but I prefer a clearer picture of what is going on between two people prior to meeting up. If I ask someone out in person, I simply ask if I can buy them dinner.
Simple. Clear. No questions.


But anyway, I was thrown a bit off gaurd by the experience, but overall I wouldn't have acted differently or anything. I just like to know what I am getting myself into. I am not one of those people who act differently on a date, I'm very picky about being myself, but I do like to have a plan when I go on a date. For instance, if we are going to dinner I like to have a few backup places in mind that are close by, and some dessert or bars close by incase things go well. I think I'll just have to be clearer when I make arrangements about such things. In addition, I like to pick venues that are a bit less causual and more intimate.

Other than that the date wasn't very interesting. We didn't really "click", which wouldn't have bothered me as much if I knew it was a date going in.

Craig's List of Women

I decided if I was going to do online dating, a traditional online dating site like match.com or that other one that escapes me at the moment may be too commercial for dating a wide variety of people. So I started my online dating search on www.craigslist.org. Now, many people have said that this is the worst place to meet people, but I'm hoping for some diamond's in the wrath. I figure by only replying to posts, its a little less absurd since I can pick and choose.

So far, I've sent 7 emails and received 2 responses. Interestingly, both responses were from posts that were more looking for some fun times in the city than a relationship per say. This is probably one of those things that will build my character, but also puts a damper on a "date" themed evening.

The first woman to message me back, lets call her "Girl A", included some pics, but the email was quite brief. The shortness of the message put me off gaurd a bit, guess it felt more like an interrogation. Anyway, being curious, I googled her name and her facebook profile came up. Her picture was one of the ones she sent me, but in the other pictures she looked quite different. Now, I know people want to post pictures where they look attractive, but this girl looked straight up different. This puts me off a bit. I mean do people really think that when they finally meet up the other person will suddenly have a change in taste? Doubtfull. To me it suggests that the woman doesn't think she looks good enough to get someone worth dating, or isn't happy with her looks. Now there is nothing wrong with that, but there is with misleading people. A lot of people aren't happy with their looks (myself included), but that doesn't mean you need to be sneaky about it. What else would they be sneaking about?

The other response I got back really surprised me. I got a pic, and it turns out she is of a different race than myself. I've never dated someone of another race, mostly because I think I have a harder time connecting with other racial identities. I'm not naive enough to think that my social circle is well diversified, quite the contrary actually. I'm definately guilty of self-segregation. But like I said in my first post: this is partially an experiment, so I might as well see if we get along. Who knows? Maybe we'll get along really well. I'm rather excited about it now, actually.

Online Dating

I think a most interesting place for me to start is dating online. Now, a lot of people (including myself) find this creepy, desperate, and just.... wrong? But the truth is for all the weirdo's and creeps out there, everybody knows somebody that it worked for, so I guess it can't be that bad.

In addition, I want to avoid dating people who I know, or who know my friends. This reason is two fold. First, since I want to go on dates to get to know people, dating all of my friend's friends could be a disaster, and look bad for me and my friends. Second, asking a friend or associate out right out of the blue could cause awkward repercussions if the mis-understand your advance, or aren't interested.

That being said, its my goal to date people who none of my friends or associates know. As such, starting online may not be a bad idea. I'd like to get the ball rolling as soon as possible so that I don't disappoint you, my loyal readers.

So off to the internet it is!

Welcome Singles

Hello and welcome. This blog is to track my experiences in the dating scene in Philadelphia, PA. I've started it partially as an experiment, and partially as a way to reflect upon the adventures I have decided to embrace. I am going to keep the posts as anonymous as possible, as I think thats only fair to me and the other parties involved. I'm a single mid-twenties male living in Philly, and decided after a long-term break up and some close friends moving away, it was time to start dating. Not just like oh, "now I'm available" dating, but tossing out the bullshit and straight up taking women out to dinner and all that jazz. I enjoy going on dates, but think I don't go on enough of them, kind of like how you always feel like you should eat sushi more often. I'm not out to mess with anyone, or be cruel, or talk trash about people on the internet, but I'm out to chronicle something that I think will be interesting, and something I should reflect on. I know what I am looking for in women, but someone once told me its a good idea to date someone you think is wrong for you. We're not talking about relationships, just a single, honest, laid back date. So that being said I'm not going to be too picky in who I go out with, so long as they are good company, why not give it a try? If I find the right person for me in the process, great, if not, at least I'll have had some good (hopefully) and interesting (probably) experiences for it. Ultimately I'm searching for a long term, involved relationship, but for now I think I'll enjoy not having one for a while, and maybe make some new friends in the process.

So here it goes, Philly. I'm going to give it a go. I predict the hardest part for me will be not getting discouraged, so if you found this for whatever reason please feel free to comment, as even constructive criticism makes me think about things more.