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Venn diagram of drive-by dating

At what point do the dating sites become “next exit” signs in the world of high-speed relationship highways?

A couple weeks ago, I received a few promising messages from someone named B. We took the leap and crossed from messaging into phone texting. Then one evening after a lull, I get a message from B. that read: “Sorry that I might’ve led you on, but I started dating someone recently and I think I want to be with him. Good luck!”

I let out a breath as my ego momentarily raged.

The facts: we’d been messaging rather nicely online and via text message. Never met in person. But yet B. was dating someone else. And in the space of a week, I was told goodbye.

At what point do you remove yourself from the online dating space when you’ve begun dating someone?

Do you filter out those people you just aren’t that into? Sometimes, the water is murky.

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Wait, I know this address…

Hook-ups happen. Especially in this age of social media sex. So imagine my surprise when one impromptu Saturday morning, I decide to pop over for a romp with someone whose abdominal muscles I couldn’t pass up, and the address I was given turned out to be the same address of someone I had intentions to date once the year before.

At what point do we start repeating ourselves?

Living in San Francisco means small spaces. We’re packed within seven square miles, and none too close. Everyone knows everyone. And sometimes, those we know live with those we want to sleep with.

Upon entering, I tried my best to shield my face and disguise my voice when I realized I had to play gracious guest with the former fling while in the hallway with my hookup.

Did I worry that said former fling would text our mutual friends and call me a whore? Briefly. But I was more worried about how many that might’ve happened and I wasn’t aware, with my previous roommates. I lived with two other gentlemen of similar age to me, and god knows how many hookups we’ve all had between us three.

Is the endless loop we all go through some form of purgatory? I strongly doubt it. I think it’s a matter of deciding whether to make different choices in the face of judgement.

But bravely I marched on, towards the bedroom that morning. And I took my clothes off as smartly as I would have had it been my first time in that place.

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I’m late, I’m late for a very important date

"By all means move at a glacial pace. You know how that thrills me." Truer words never spoken, especially in the context of dating. There’s an understood code of arrival timing for both parties. There’s also an understood period of when "late" is.

Now imagine waiting for two hours for someone, for an originally 8:00pm hotel date and here you are, 10:00pm, still walking around. You could get a drink, walk around, waste your attention on Angry Birds or texting inanities. But it’s not really by choice you’re killing time.

When it comes to timing, when does late become unavailable?

There’s always a moment when one has that internal pep talk: I’m better than this. I’m going to give him until 9:00. Actually 9:15 just in case. Damn it, 9:30 because I took the bus all the way down here. And isn’t this cardio, all this walking!

Just from conversations with others, we all compromise our patience for the sake of getting laid. Is that 30 minutes delay really worth going to third base? How long would you wait to slide to home? If it gets too late do you get to stay over or trek back home?

Now imagine that at 10:00 as you’re getting on the bus back home, in your date jeans and glossy hair, and you get the following SMS:

Wanna 3way with this hottie I’ve been msging with at another hotel?

I’m sorry. I have to wash my hair and brush my teeth.

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The tight rope cakewalk

Far too often we find ourselves walking that very thin line with a potential mate between next date and not until the next lifetime. We start the song and dance portion like a cakewalk; slowly we revolve around the chairs, waiting for the music to stop so we can grab an empty chair and win the game.

Very recently, I was out on a few dates with V., and thought it was headed towards relationship land. But when a tentatively planned frolic turned into a “I’m already busy. All day. And all night. Maybe we can talk next week?” then that precarious balance was thrown.

What’s the right foot forward in this balancing act of dating?

I discussed this over champagne and some early March sunshine with G. and G., a newly minted couple that I’ve had the chance to watch their courtship turn into a relationship. Something G1 said to me, stuck a chord. We’ve all heard the modern adage: maybe he’s just not that into you. There is truth that if someone really wants to see you, they’ll make time. It’s like time is the most precious investment next to money. We all need more time— we’re so busy that we leave little to leisure. I know that if I’m kind of meh about someone, I’ll weigh my options around seeing them, and keep myself distant. I’m not proud of it, but liken it to something like prioritized scheduling. Do I really want to spend more of my time with someone I don’t think I’ll spend my life with?

It makes me wonder: If you don’t attach a large amount of personal value, then isn’t it viewed as cheap time spent?

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Get over the ex by getting under someone else

Far too often do our friends mirror our own hopes and horrors, especially the pathos of relationships. Either we wistfully yearn for them and the storybook romances, or we wince and secretly thank ourselves for not headbutting our way into that sort of doom and gloom drama.

So at what point do our romances and bad romances just become fairytales?

Two friends of mine, R. and J., sat down with me before the New Year at an outdoor pub to discuss the ins and outs of their receeding relationships. R. had been in a relationship where both he and his partner living together since day one due to circumstantial events. Now, R.’s boyfriend wants long term space, meaning R. is stranded in limbo looking for a place to call home and a new lover. J., on the other hand, entered a very healthy relationship (whom I envied for a bit) that’s now verging on the tailend of a break-up due to boredom, of all things.

While both have completely different sets of problems, they share a common theme: their significant others held all the power. R. allowed his lover to be house host instead of keeping independence, whereas J. let his relationship get stagnant. I, myself, was broken up with by a long-term potential who saw the expiration date much sooner than I did. Now that we were all forcibly single again, we had to come to terms that our happy endings were getting an edit.

Yet strangely, all three of us were determined that in order to get over our woes, we needs to get under someone new. Is sex with someone new post-breakup the new remedy to a broken heart?

Consistently I get advised that the best way to get over someone is always extended distraction. Eventually enough distance gets between you and the former to get friendly with the new guy/gal. Many people call this a rebound…I call it a refresher in what I’ve been missing. Why waste time on making sure your ex knows your wrath for having given up on you?

Being scarily angry all the time isn’t good for the complexion, nor the social disposition.

J. and R. agree.

As traditional relationships go, one hears about the post-breakup limbo— where showers aren’t taken, beds become home, and mourning becomes a daily occurance until something magically happens and suddenly you’re able to live again. As a 20something who enjoys his social life (and bathing), I’d rather keep myself “out there” and stay current.

It’s such a shock to the ego when you are gone from the dating world for any extended period of time. New people arrive on the scene, as well as new rules and restaurants to be seen/heard at. You also start the damage control: everyone knew you were in a relationship, what happened?

So it’s a rather lovely blessing to bump into someone accidentally that you know you’ll be able to bump into behind closed doors. Isn’t that what dating is all about?

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The text mess

Rather recently, a week ago, SP had been SMSing with JC. It appeared that the LOLing was going to turn to XOXOing, but as luck would have it: it all KOed.

How much are we date texting that we miss the actual context?


Most conversations amongst the 20something crowd now involve some form of text message. God forbid we actually use a phone call, since we’re always at work, bars or toilets. We use 140 characters to fulfill the need to communicate, especially those we find sexy.
Some take it to the point of sexting while in business meetings, others use it as a medium to plan dates. But when a textual conversation leads to standing someone up, one has to think:

Did the absence of actual conversation become the 140-character buzzkill?

SP got stood up, plain and simple. All it took was “It’s going to be a hassle to get down to where you are. Plus I’m at dinner with my friends.” And in retrospect, over vegan doughnuts, SP said that the hurt feelings stemmed not because it was a blow-off, but because it was through a text message. Methinks that in the age of tech, conversational grace should be taught.

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The numbers game

"You’re a 7. On a good day." Earlier this evening, I was chatting with a stranger I’ve noticed a few times, trying to be witty and we got to talking about where we rate on the 1-10 numbers scale. I asked for absolute bluntness (as a stranger is more willing to be truthful than a good friend will in lieu of hurting one’s feelings). Yet somehow I wasn’t prepared for the pit-fall in my stomach when said stranger said that comment with no reservations.

Why does a single, subjective number seem to outweigh even the most important of factors?


And more importantly, how does that rate in redeemable qualities?
I grew up knowing that I wasn’t like the other boys, but somehow I grew into something that suited society’s perception of physical attractiveness. Having always felt like I was slightly out of sync with the rest of the world, beauty comments resonated, as they do with anyone who has felt less than modelesque.

When you’re told you’re a 5, does that only make you halfway to beautiful?

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Photo credit: Wired.com

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What came first- the booze or the bed?

Over an intense online discussion with a ladyfriend in LA about the travails of dating multiple people, we touched upon the painful secret we single(ish) people all share- more drunk sexytimes than sober.

C., who isn’t promiscuous by any means, told me that she was mortified by her boozy behavior and couldn’t remember a recent time that she was sober in bed with someone, and it got me thinking:

If alcohol gives us liquid courage to go to bed with someone, and it also let’s us do things with people we wouldn’t normally do, does being sober make us intelligent cowards?

Going out to a bar is always panic-inducing, especially if you’re alone and you’re driving. We use alcohol as a way to ease into that awkward aloneness. It opens us up to new experiences and conversations with people; a crutch if you will. So what if during your boozing you spy someone that at the moment is considered attractive? I’m the first to say that I’ve done it— hit someone up that during daylight hours, I’d be more reticent to unbutton my pants to. We make these choices though…regardless of our inebriation.

And then comes the regret. “Who is this guy?” “What happened last night?” Questions like that leak out of our fuzzy heads in the a.m. when we’re scrambling to put ourselves back together.It’s always the retrospection that bites us in the ass.

In bar politick, when does trying to get someone in bed become bad?

Then again, what would have happened if you were sober? Not much better- you’d be going home alone and chances are you didn’t have a good time. I’m not saying that fun MUST be had with alcohol, but if you’re nervous about meeting someone, that sharp scrutiny on your own self-consciousness can hinder the flow of casual conversation. It can also make your arousal decrease once you’ve taken your clothes off with that person. That nagging inner voice that says your body isn’t good enough to be on display can definitely put a damper on feeling sexy. HOWEVER- you’re not regretting any boozy mistakes, and definitely curbing your risks of STDs and kinky(er) sex.

C., as a heterosexual female, is definitely for the wiser in recognizing destructive behavior before it gets too out of control. It’s definitely more dangerous for a good-looking female at a bar full of men, who also happens to be drunk. But she brings up a good point: are we as a society programmed to accept drinks as bribed entrance to our beds? Is that the new sexual currency?

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The straight shot

When does being one thing bleed into the next while in bed? I had the most unusual experimental experience last night at 2a.m. with an Aussie who was heterosexual. A very attractive blond and physically fit, he happened upon my profile on one of those sordid dating sites (begins with a “g” and should have air quotes around it) and messaged me.

He was in aspects of the word, straight. He dates women, loves women and has never done anything physical with a man. Yet he was in an impulsively adventurous mood, and decided he’d like to give the gay a go.

He told me that he’d like to massage me, and far be it for me to decline. He had good hands. Clearly it got more physical after that, but we didn’t finish and instead turned to naked conversation. I was impressed with his lack of nerves, as this was the first time he’d been physical with the same sex. He was quite complimentary (cheers to my fitness regime) but said that he satisfied his curiousity. However what struck me was that he was very confident in his sexuality while toeing the line.

When did blazing the trail for one’s identity become such a casual frontier?

It was an interesting experiment on both ends— he with another man, and I with someone who while attracted to me, was not like me. It got me thinking that the fluidity in our sexuality or at least bedroom identity may be more ambiguous than we’re led to believe.