We held off on this one, since we figured not that many first dates were happening on Valentine’s Day. But now here we go. OKCupid, always ready with the best questions for blog posts, asks, what are the best questions for first dates? Actually, they put it a much better way: “What questions are easy to bring up, yet correlate to the deeper, unspeakable, issues people actually care about?” Yes! Easy and deep-y. And did we mention easy? See, because what you don’t want — as with first “lines” — is something gimmicky, interviewy, or otherwise annoyingy. (“So, tell me, Sam. [Leans closer, significantly.] Would you rather be a cloud, or a grape?”) What you want, OKCupid determines, with the use of several handy bar graphs, is “the shallow stuff to ask when you want to know something deep.”

OK SO LIKE WHAT? Well, then we get into some frankly fascinating correlations (derived from their vast database and some fancy math). If you want to know if you two have long-term potential, ask if he/she likes horror movies, or would like to chuck it all and live on a sailboat. Couples who agreed on such Qs were correlated with couples who lasted. If you want to know if your date is religious, ask if she/he is annoyed by spelling and grammar mistakes; “If your date answers ‘no’—i.e. is okay with bad grammar and spelling—the odds of him or her being at least moderately religious is slightly better than 2:1.” Hooray for teh tolerance! Want to know if you have the same politics? Ask if your date prefers the people in his/her life to be simple or complex. The latter preference is correlated with liberal politics. JUST SAYING. (Also: clouds and grapes CAN get along!)

Read the whole piece for great fun and info, plus Kevin Costner in fingerless gloves. (The apocalypse kind, not the golf kind.)

AND: Since you’re going to need to get to that first date in the first place, here is BG’s definitive guide to opening lines.

Mad props to OKCupid:

Gay issues have been in the news a lot lately, from the debate over same-sex marriage in Congress to a sickening rash of gay-bashing here in New York City. We see a lot of emotion out there, instead of information, and we wanted to provide some data-based context on sexuality so that people might make better choices about what they say, think, and do.

We run a massive dating site and therefore have unparalleled insight into sex and relationships. Here’s what we’ve found, in numbers and charts…

Their data-based results include: gay people are not out to bed breeders, gay people are not “promiscuous” (even on a dating site), and a whole lot of people are gay-curious. (BG: Possibly, in some cases, those who are gay-furious.) Anyway, just go read it. It’s quite important, and also very funny. That’s it. I just wanted to give the report, and its mission, an even bigger high-five than I could in 140 characters. VOTE CUOMO!

As Amy noted earlier, Christian at OK Cupid’s blog recently found, using all sorts of lovely charts and graphs, that  “the male fixation on youth distorts the dating pool.” Maybe so, but I have an observation — or maybe a confession — to make: The fixation on youth isn’t just male. While it may be represented as such online, there’s still a whole lot going on offline. Since moving to New York almost 5 years ago, I have, ahem…well, I have developed a habit of dating younger men. Before living here, I mostly dated older men. Why the shift? Is it something in the water?

At the ripe age of 31, while staring into space writing at a coffee shop, I noticed a guy looking at me rather intently. He caught my eye, smiled furtively and then took a swig of his grande. I smiled back and continued about my business. The next time I looked up, his eyes met mine and he executed a rather sheepish wave of his hand. Within seconds he was sitting in front of me and by the time I left, a date was planned. About four dates in, we met up with one of my friends for drinks. Somehow the subject of age came up.

I figured he was younger from conversation and just how he carried himself. I’d also dated a 22-year old the summer I was 29, so when coffee shop guy told me he was 26, it didn’t faze me. What I wasn’t expecting was his reaction to my age. At first it was incredulous disbelief. Had I no proof of identification and a friend to verify, he wouldn’t have believed it. He had guessed I was 24 or 25, but suddenly it clicked. I was confident and self-assured, had lived on my own in quite a few places, and pursued various interests. I wasn’t 25 or even close.

Suddenly he made assumptions about what I wanted: something serious, marriage, babies. Like, with him.By next week. It didn’t matter that we were on date number four or that I was just out of a tumultuous relationship. In his head my age screamed entrapment. Like I was ready to drag the first guy who smiled at me that morning to the altar. Needless to say, our date was cut short and the warm goodbye that ended our previous date was replaced with a very reticent hug.

While looks have something to do with attraction to the young and virile/fertile, maybe the reason per Christian’s data that “the median 30 year-old man spends as much time messaging 18 and 19 year-olds as he does women his own age” is not only about physical attraction. What might also be at play is what those men want at the moment and what they perceive rather than just cut and dry looks. People seem to think that once women hit a certain age, we’re on this warpath to the altar or the birthing center. Yes, we have a time limit with reproduction, but we already know that and a lot of us make peace with it one way or another. However, we don’t have an expiration date when it comes to love, lust, spontaneity or enjoying life. We also don’t want to marry and make babies with everyone we go out on a few dates with. While we are more likely to be looking for a real relationship, we also like to meet new people and explore our options. What we don’t want is a constant reminder of how old we are and questions like “shouldn’t we be finding that special someone soon?”

For me dating younger men has been an eye-opening experience. At first I found myself drawn to them because they are cute and fun, but that’s not all they are and that may be a common mistake when going younger – the seriousness factor. The men who are choosing younger women are potentially not doing so at a disservice to older women, but possibly as a disservice to younger women.

When I dated a 22-year-old at 29, I embraced the experience. Surprisingly, fitting into each other’s worlds wasn’t actually that much of a stretch. What I was surprised about was the reaction from my friends, particularly my female friends. A lot of them voiced some concern because 22-year-olds wouldn’t want to get married anytime soon. That was just it. At the time, I wasn’t ready to get married. I was running far away from commitment and wedding freak-outs. Dating a 22-year-old was safe.

In terms of OK Cupid’s data, I would like to see a chart comparing what exactly each person is looking for – like are the 30 year old men who are messaging 18-19 year olds looking for a relationship or a “playmate”? Odds are, they are not looking for a life partner. As such, young women as a whole may be getting the short end of the deal in terms of their interactions with much older men. They may not be taken seriously or seen as viable long-term partners. Maybe the disparity between men and women’s dating habits with regard to age in the OK Cupid data is just as much about emotional age as it is about physical attraction. Hell, if those men need convincing that older women can be as full of fun and energy as a younger woman, then maybe older women don’t want them anyway.

My point is we often date people we think we might not get serious about when we are not ready to be serious –- which is fine, but we should also be open to the possibility that someone will surprise us. What I’ve learned as I’ve returned to a place where I am ready for a relationship is that men of all ages can be both fun and serious, thoughtful or thoughtless. Internet dating eliminates nuances as it makes us all check a box, but it’s only reflective of what we as a society already perceive. It’s time older women and younger women alike get as much credit for their whole person and not categorized by stereotypes of age and gender.

The brainiacs over at OKCupid — a dating site incubated by a bunch of Harvard math geeks in ’04; also where I met my music-nerd future-hub in ’09 after being a member for all of a 48 hours — recently crunched a few numbers to analyze the effectiveness of users’ profile pics. (Effectiveness = how many contacts were received monthly.)

What they found, which they’ve published in a lengthy, graph-dense screed, blew them away: “In looking closely at the astonishingly wide variety of ways our users have chosen to represent themselves, we discovered much of the collective wisdom about profile pictures was wrong.”

Specifically:

* It is not better to flash a pearly grin; instead, keep lips sealed and upturn your mouth corners coyly-yet-half-assedly. Females should do this while making “flirty eyes” at the lens; males should do this while gazing off-camera.

* By all means, do use a self-shot pic taken on a cell or webcam; what you forsake in high-pixel polish you’ll recoup with “an approachable, casual vibe that makes you feel already close to the subject.”

* Chicks especially can cash in big-time with the cell/webcam pic’s stylized subset: the  “MySpace shot,” which even OKC can only put into words as “taken by holding your camera above your head and being just so darn coy.” Like porn — which, c’mon, that’s what the MySpace shot is, right? First cousin to an American Apparel ad? — it’s hard to define a MySpace shot, but you know it when you see it. And when dudes see it, “the MySpace shot is the single most effective photo type for women,” annihilating the second most effective (in bed) by about 3-to-2. (And it’s not just because of the shot’s down-the-shirt angle, according to OKC’s stats.)

* Males fare better not wearing a shirt than wearing one… gah, hard to read much past this without short-circuiting my keyboard with the tears I weep for the future. The second half of the article talks about how old dogs (i.e., me, 35yo) should not learn these new tricks, as the backfire ratio swoops skyward the older you get.

AKA, OKCupid is not OK for “cougars.” Unless (and yes, I unfortunately do speak from experience here*) you do not mind being bombarded with IM requests from Fordham sophomores (and UPenn juniors and NJIT frosh…) to come see their dorm rooms tonight, because they’ve slept with tons of older women and they know just how to push your buttons and maybe they can show you how to use a webcam since when you were born phones actually had dial tones.

* Actually, it was pretty entertaining chatting with them.