The Year of Living Dangerously Part I: Ray Tries Online Dating

Surely you might think that this is a lame way to begin "The Year of Living Dangerously". And I've clearly tried to danger it up in the title graphic. You probably thought that I was going to start off with base jumping or Russian roulette or spelunking. Maybe you were thinking hang-gliding...or as I like to call it: Suicide Kiting! You most likely thought I’d be telling you about some grandiose adventure that I was going to embark on. Well, let me assure you that any date that I go on is a god damn adventure. You’ve never seen a night fraught with such peril as Ray trying to impress a girl and show her a good time. It would be safe to say that I’ve been out of the serious dating game for “a while”. I haven’t made it to Date #3 with a girl in over five years. Online dating seems like the most efficient route to try and stamp that streak out. Online dating has a less than preferable rep in some circles because it’s not the way that our parents did romantic social interaction and there is the perception that dating websites are the refuge of the fundamentally and irreversibly flawed. Well, I myself happen to be fundamentally and irreversibly flawed…so I’ll fit right in.

The first step on this journey of a many miles is to select the proper vehicle with which to pursue the fairer sex. There are tons of online dating sites and I need to select the one that will deliver the most promising results. I’ve already eliminated J-Date, FarmersOnly, and Ashley Madison because I’m not Jewish, an aggie, or a home-wrecker. I’m going to eliminate Christian Mingle because, while I am Christian, Christianity in no way defines what I’m looking for in a girl and I’d like to cast a broader net. I’m eliminating Plenty of Fish because it has a desperate sounding name. And I’m eliminating Craigslist because I have zero desire to end my date night with one wrist cuffed to a radiator in preparation for my organs to be harvested. After carefully perusing which sites I should obviously not be going with, there are three that are left: eHarmony, Match, and OKCupid. From here it’s an easy decision. Match and eHarmony expect that I should pay to be rejected by their women. I can assure you that I am perfectly capable of being rejected by women for free…thank you very much. OKCupid, it looks like it’s you and me.

So, we’ve come to me needing to put myself out there to try and reel in the ladies. I’ve got to cast some bait…some flirty, sexy bait. And with talk like that I probably should have joined Plenty of Fish. Lying on this web site will get me nowhere. I need to be myself but there’s no reason that I can’t try and be the better, more upstanding version of myself that I’m capable of being. It just needs to be a sustainable me. I need to be comfortable. Trying to show a girl the best Ray that I can be will get fucking exhausting by the second date. The trick is to try and be a better person while also letting them see what they’re getting in the long term. Take my 20 most recent pictures. Throw out the 5 best. Throw out the 10 worst. Boom! Presentable but not misleading. I needn’t try to appear better looking than I am. It’s far better to weed out the shallow ones online, so when I get a hit I can be confident that the girl knew what she signed up for. Don’t talk about my job at all. It’s boring as fuck and I don’t want her to fall asleep while reading my profile. Keep my interests and hobbies real but try to highlight the ones that we might have in common. Chicks love to hike. Fewer chicks like to golf. Keeping both of those in the hobbies section is fine but talk up the hiking more to play the percentages. I don't mean to disparage and over-simplify my own gender, but I'm going to. Men are not terribly complicated to understand. Whereas, the male population will tend to gravitate towards the same type of female profile...women tend to have more diverse interests. But that doesn't mean I shouldn't try and play percentages.I should seem educated and open-minded. By posting honest pictures you’ve already established that you’re not after a girl looking for a mindless meat stick with great abs. (They wish that's what they were getting.) I want a girl that will appreciate the better qualities that I actually possess. I'll have opinions to appear less generic but let them know that I'm flexible also.

Now it’s time to select a girl. Merely having a profile might attract a few moths to the flame, but if I’m waiting for Princess Charming to come and make the first move…then I’d have been just as well off not joining an online dating site in the first place. I’ve narrowed my selection criteria: aged 23-32, within 40 miles of my home, preferably been to college. I’ve read through profiles and carefully minded people’s answers to the list of questions presented. I’ve found several girls who are interesting. There might be one or two that I’d ask out before the others but my selection criteria has gotten me nowhere thus far in life…so why should I trust it now. For this to be a true adventure in the spirit of The Year of Living Dangerously, I can’t just pick the girl that I think I’d be most comfortable with. And I sure as hell am not going to leave it up to fate or chance…that fickle bitch. I think the requisite course of action is to put the decision in the hands of my readership. Below I have selected five girls. Each of them are described in 50 words or less and are presented with a unique alluring feature and a warning sign. To vote for which one I should pursue first, please post your thoughts in the comments section. I'm well aware that given response rates, I'll probably end up contacting all of them. But I want to see where you're heads are at. And in the event that I do get multiple responses, I need to know where to focus my initial efforts. 

Lady #1: Career-driven Boston girl. She's Catholic and fairly religious. She's working on her MBA. Her tone is fairly sassy but well-spoken and intelligent. She's clearly into sports (especially baseball) but also markets herself as a girl's girl. She is interested in kid's and her long-term life aspirations sync well with mine.

Alluring: Her political views and discourse appear similar to mine on all fronts.
Warning: She has dogs and has little interest in a partner who isn't interested in having pets.

Lady #2: Free-spirited Jewish girl from San Francisco. Profile is a little all over the place but not in an obnoxious way. Very artistic. Enjoys painting and the such. Doesn't seem to be in to outdoor adventures, camping, or roughing it. Seems to like guys that are clean cut ala Don Draper.

Alluring: Definitely has a good sense of humor and is not afraid to be offensive.
Warning: Worked for the circus for a few years, we're dealing with a carnie.

Lady #3: Bay Area girl. Teacher and aspiring writer. Family appears to be important to her. She's very open about what she wants even if it's not completely politically correct. Very well-spoken and intelligent...I even had to look up a few references from her profile. Gives off a counter-culture vibe.

Alluring: Clearly very attractive based on pictures and lives an active life.
Warning: Seems to be a little out of my league and knows it.

Lady #4: Extremely well-traveled, bilingual, self-proclaimed nerd. Works in the fashion industry. She's an excellent cook and is very extroverted. If OKCupid's rating system is to be believed, she is also more competitive than me and more adventurous than me. I'll believe it when I see it.

Alluring: She's a big Kings fan, and hockey fan in general...as am I.
Warning: She travels a lot for work. China, Denmark, you name it...she's often on the road.

Lady #5: Very frank and forward social worker. Is originally from Southern California and is still very close with her family. Strongly Christian. Is an avid runner and appears to enjoy all sorts of outdoor activities. Is two years older than me, but is looking for somebody younger.

Alluring: Has dabbled in stand-up comedy...as have I.
Warning: Graduated from USC...so I can't take her home to meet mom and dad.

I will make first contact with whichever of the following ladies you, my readership. deem most worthy by the 31st of March. And any date that comes about will be reported on in a future blog post. Please note that this bottom section may likely be removed on March 31st as my potential dates will possibly be internet stalking me.