(Originally appeared on AskMen.com as “Blind Date Advice,” Jan 2012)

While working for a cable TV network four years ago, I somehow landed two free tickets to a stand-up show at New York’s Gotham Comedy, and decided to invite my childhood friend and fellow comedian, Dave. At the event, we were rushed to the head of the line and seated in the front row with complimentary cocktails as VIPs. I could sense the audience puzzling over the identity of the young gay power couple that had just entered the room.

Later, over a few more drinks (or six) at his place, Dave revealed what had been stumping him all night: “Dude, thanks for the show – but why would you invite me when you could have impressed the hell out of a chick?”

He was right, but it was too late to take his ticket back. We did conclude, at least, that we should both be better employing our assets to impress girls. In fact, we reasoned, as two funny former improv troupe teammates, we could probably kill it if we joined forces.

So that night, Dave and I uploaded a YouTube video in which we described our interests (e.g. making money, walking) and requirements (e.g. STD-free, legally sane). Twenty minutes and six views later (thank you, “refresh” button), we learned our first of many lessons in internet dating:

1) Market yourself. 

Without advertising, how else were women supposed to find our video? I suggested that we post an ad on New York City’s Craigslist highlighting some of the many positive qualities our Grandmothers had always admired us for (e.g. handsomeness, height, the ability to lift extremely heavy things) and some they had not (e.g. modesty).

Within hours of publishing the ad, we had already learned a second lesson:

2) Expect a challenge.

Messages began to pour into our new joint email account – most of which were from seemingly imbalanced women who type in all caps. Plenty weren’t from women at all, such as the gentleman who proposed that we “both bend [him] over and take turns slamming [his] butt.” All of our friends told us we were nuts – some, because they were secretly jealous; most, because they thought we were nuts. For obvious reasons, we refrained from telling our sweet, Jewish mothers about the mayhem overflowing from our inbox.

Merely one week into the project we’d amassed hundreds of potential love matches, but had yet to capitalize on our bounty. So we sat down and wrote back to a cute Brooklyn pair who seemed least likely to murder us. Once they had approved our proposed plan, Dave and I laid out a few ground rules for the evening (i.e. he wouldn’t liken me to a “poor man’s Tom Hanks,” and I wouldn’t talk about him shaving his feet in high school) and met the ladies at a laid back Williamsburg pub.

With introductions barely underway, I noticed the waitress creeping up on our table, gesturing to politely interrupt. “I’m sorry – but are you Dave and Ethan?” she finally interjected between our awkward sips of water. I repressed a spit-take and saved our equally shocked dates from a dousing, water now dribbling unsexily down my chin.

“We are,” Dave responded, barely suppressing his pride for our entirely undeserved celebrity.

The waitress smiled as our dates stared at us, slack-jawed.  “I thought so. My friends and I have seen your video.” She walked back into the kitchen.

“Do you get that often?” one of our companions asked.

3) Never take a gift for granted.

“Oh, you know…sometimes,” I lied terribly.

That first date continued to go fairly well until, due to nerves or a lack of interest, we bailed on what was about to become a dual make out session (alright — we totally panicked).

4) Again, never take a gift for granted.

Perhaps out of spite, one of the girls “pranked” Dave the next day by accusing him of impregnating her (our first immaculate conception) as her friend cackled in the background. Did I mention these girls were young?

5) Screen, screen, SCREEN your dates.

Not as young, however, as the girls who posed as 21-year-olds, only to reveal their true age (*cough* 16) when producing workers’ permits as ID at our first bar stop of the night. Nor were either of them as crazy as the meth-addicted ex-soft-core-porn-star who attemped to force her way into my apartment despite repeated denials. Nor as drunk as the vodka-swilling, filthy-mouthed military chick who stole my watch and a bottle of whiskey before running off for a threesome with Dave and her friend, leaving me passed out alone on the couch in my underwear.

6) Pace Yourself. 

After dozens of New York engagements, Dave and I decided to expand to other cities. Soon, thousands of emails had arrived from Boston, Philadelphia, Los Angeles…even London and Sydney. We would eventually entertain over 200 dates, and our experiences were translated into a live comedy show at the People’s Improv Theater. The “educational” show became popular with college students and gave way to a national tour, allowing us to perform at hundreds of schools across the country over the last three years.

In our quest for romance, we’ve learned plenty. But perhaps no lesson is as important as this:

7) Look out for your wingman.

Because in the end, friendship almost always outlasts love.*

(*Dave forced me to include this one.)

(Originally appeared on YourTango.com, Jan 2012)

On a whim a few years ago, my friend Dave and I posted a YouTube video in which we invited women to double date us. In the months to follow, we would embark on over 200 double dates together, many of which would provide us with horror stories for a live comedy show. However, none were a bigger disappointment than one I experienced on my own.

As usual, it started with an email:

from: tres bien ****@gmail.com
to: daveandethan@gmail.com
date: Sun, Apr 6, 2008 at 8:56 AM
subject: two can have a party

all of my girlfriends are taken.
but ethan, you are adorable.

Finding the email quite sweet (but still scarred by the “naughty 21-year-old college beauty” who turned out to be a 16-year-old high schooler with a worker’s permit for ID), I cautiously wrote back:

why, thank you.  feel free to send a photo, and if we find another single “dave fan” we can have ourselves a party. (dave and i promised each other we’re only doing doubles until we both find love.)

-e

She sent a photo within hours: a strangely expressionless but attractive close-up, her face illuminated as clear as day.

Quickly changing policy (but still scarred by the “fiery 22-year-old Latina” who turned out to be a 45-year-old Puerto Rican transvestite), I secured her number and called the next day. Following a long, casual conversation about mutually adored music, books, and movies, I wrote the following playful email:

ok.  here’s what needs to happen:

you’re going to move to ny.  preferably this week.  then i will completely bail on my plan with dave and single date you myself.  screw him—honestly, how many friends do i really need?  then, after dating for a few weeks (days?), we can elope.

i propose this all based mostly on the fact that you are incredibly cute.

does this all work for you?

-e

Here is where I made my first mistake, and learned an important dating lesson: Never joke too aggressively with a blind date. Little did I know, I was inviting disaster into my home…. But I’ll get to that.

Over the following week, we engaged in written correspondences filled with flirtation and sexual tension. The excitement came to a peak when she revealed her prior “occupation” over the phone one night:

Ethan: Well, a desk job isn’t inherently bad. Why don’t you like it?
Tres Bien: It’s just so boring. Way more boring than my last job.
Ethan: Which was…
Tres Bien: Are you familiar with Suicide Girls?
Ethan: (long, astonished pause) YOU’RE… A SUICI – Yes. Yes, I believe I’m familiar.

For those who aren’t familiar, SuicideGirls.com is a softcore porn website that features goth, punk, and indie-rock women – often heavily tattooed and photographed in the style of 1950s pin-ups. In other words, dating a Suicide Girl is a former Magic-card-playing, Fugazi-loving emo-teen’s dream come true. I needed to meet her.

Which illuminates the lesson learned from my second mistake: Never fixate romantically on one aspect of your date. Becoming infatuated with a person because of one idealized element of their personality will spark nothing more than inevitable disappointment. However, when a man is gifted with sexy nude shots, lapses in judgment are not uncommon.

So I invited her to take the train from Philadelphia to New York City for a date I’d plan. With that established, I learned more about her via Gchat throughout the week:

Tres Bien: I used to do drugs when I was a teenager
me: Drugs? Like crack?
Tres Bien: Haha no
me: Meth?
Tres Bien: Um…let’s talk about this later ok?
me: Ha, OK. But can I call you Methy McGee?
Tres Bien: No. It’s kind of a touchy subject for me
me: Oh. OK. Sorry
Tres Bien: It’s okay… that’s why I wanted to talk about it in person.

And there was yet another interaction I failed to assign a red flag to:

Tres Bien: so.. if i cant find somewhere to sleep .. theres no way i could sleep on your couch or something? if thats totally weird just say so
me: ha, i mean, honestly, if i had ever met you even just once before, i wouldnt feel weird about it at all.  but, i feel like its a lot all at onec, you know?
Tres Bien: yeah thats fine.  i understand

But like all the others, I swept this warning sign under the rug. And soon I was waiting patiently on the steps of New York’s midtown Post Office for my future-lover to arrive at Penn Station. Amtrak running late as usual, I waited, and waited, until my phone rang at last. She was here!

“I’m here…” she said quietly, apprehensively – almost a question.

I made my way through the winding station, weaving through corridors and commuters to retrieve her, a precious gem to be plucked from a coal mine. Finally, I arrived at the track, but found no sign of my girl. A few random stragglers peppered the platform: a homeless man, a large woman in a giant overcoat, a young child and his mother, an elderly janitor…none of which resembled my amour. I stood there scanning the room again and again for a full minute until I heard a tiny voice:

“Hi.”

I turned to see the large woman in the giant overcoat. I had no recognition of the stranger in front of me, someone who had likely mistaken me for —

Oh my God. It was she.                                 

I couldn’t have taken more than two seconds to reciprocate her greeting, but a lifetime of emotions cycled through my brain in this instant. Confusion quickly gave way to shock, then disappointment, resentment, and finally, self-pity.

This girl looked nothing like her pictures.

That she was 30 pounds overweight wasn’t the issue – it was the fact that she had deceived me with outdated photos which rattled me. I’d been blindsided: hoodwinked into an evening with a different person than expected.

“Sorry I’m late,” she apologized, and I quickly realized that the reason for her closed mouth in every photo had nothing to do with the “gothy” image I had assumed she wished to uphold: from her front gums protruded what can only be described as The Greatest Snaggletooth in the History of the World. My eight-year-old cousin has a straighter smile – and he only has half of his adult teeth. Trust me, it was bad. She made Steve Buscemi’s mouth pretty.

Thus was a third lesson learned: Never. Trust. Photos.

“I…I’m sorry I didn’t see you at first. I was distracted…about…something else,” I stammered as I led her towards the train station exit.

But she had already begun walking ahead of me. Quickly. I called after her to slow down. She paused and slightly turned her head only long enough to coldly state the obvious:

“I walk quickly.”

While awkwardly dispensing directions to this out-of-towner who refused to be lead, I made the decision that I’d overlook this disturbing introduction by making a fresh start at dinner. So what if she looks a little different than expected, I reasoned. We’d already shared some great conversation – why couldn’t we share a great night together?

My question was answered at the restaurant, as inquiry after inquiry received tersely mumbled responses and eye contact was a feat rarely achieved. Despite being able to hold down perfectly normal interactions for weeks online and over the phone, she was now more inaccessible than an unwed Mormon’s privates.

I tried every approach to lighten the mood: cracking jokes, broaching ultra-casual topics, speaking more, speaking less, even impressions. (Yes, impressions. I’m sorry, Jay Leno.) But nothing seemed to dent her icy wall. Eventually, I went for broke:

“So…why so ‘touchy’ about the whole…you know, meth thing?” I asked.

At last she looked up at me, though slightly horrified it seemed – either that I would inquire again, or perhaps because she was now mentally reliving her meth den days.

“It’s none of your business,” she finally hissed.

The evasion was now too much to bear. Could it be that this whole “meth thing” wasn’t a “thing” as much as an “addiction?” And if so, could drugs somehow be responsible for her stark change in appearance and demeanor? Whatever the answers were, I would eventually learn yet another valuable lesson: When your date refuses to answer questions about prolonged use of mind-melting psychostimulants, it’s time to walk away.

After dinner we saw a comedy show at one of my favorite improv theaters, but the entire performance was a blur. I was too preoccupied with my date’s refusal to reveal a single fact about her personal life. Who was sitting next to me? She could have murdered a thousand babies for all I knew. My eyes fixed on the show, I forced myself to laugh (too loudly) while she stared deep into the abyss, her soul seemingly lost to the darkness.

By the end of the performance, all I could think about was how to get her back as quickly as possible to Philadelphia. Panic set in when we discovered that the last train had departed only minutes ago.

“So we’ll head back to your place?” she asked with a confidence that was, at this point, entirely out of character.

“Oh, it’s late, I think I’m ready for bed,” I euphemized.

“That’s fine,” she responded. “But I’ll stay with you.”

I paused, pondering the most delicate way to deliver rejection. “I thought we…kinda…discussed that already?” I smiled lamely and half-shrugged, my inner Woody Allen bubbling to the surface.

“I’m not gonna try to fuck you.”

“Whoa!”

“Well, I’m not. I won’t even come into your room, if you want. I can sleep on your couch.”

Call me paranoid or heartless, but there was no way I was entertaining the possibility of a potentially mentally ill former nude model / drug addict robbing me or, worse, hacking me to pieces while I slept. In a panic, I explained that my roommate was uptight (an exaggeration) and uncomfortable with strange guests staying over (an outright lie) mainly because he was an Orthodox Jew (if there’s a Hell, I’m going). Then I made her call every New York contact she had in her phone. Eventually she reached some male friend, ex-, or pimp, who said it would be cool for her to come by, and I walked her underground to wait for the first uptown C train to arrive.

“So. Second date?” she asked, flashing her snaggletooth.

“We’ll see,” I lied as the C train came to a stop. I gave her a pitiful hug and gently nudged her onto the subway car.

I think she waved as the train left the station, but I’m not sure – I was already running as fast as I could.

(Originally appeared on YourTango.com, Nov 2011)

In 2005, I briefly worked as a real estate agent in New York City, renting downtown luxury apartments to European pioneers, entitled college grads from Long Island, and investment bankers with trophy wives. The job – which I took merely as a means to support myself while pursuing more “noble” efforts as a rock musician – was truly fucking miserable. I was charging extra fees for products already available to anyone willing to spend two hours moseying through the Wall Street area on his or her own. My soul atrophying from the lack of creativity, I felt more useless than a condom at a nursing home.

However, I ultimately learned a lot that year — not only about the real estate industry, but about the psychology of investing as well. I discovered what comforts human beings, encouraging them to commit, and what frightens or discourages people, causing them to jump ship.

Six years later, in the midst of my longest romantic relationship to date, flashes of my real estate past began periodically flooding my overwhelmed mind. Familiar emotions such as fear, desire, anxiety, and consolation were reminiscent of those I had read on the faces of so many potential clients years earlier. And that’s when I came to realize that falling in love is, in many ways, just like investing in real estate. In essence, both processes are held together by checkpoints which can be as stressful as they are gratifying:

Pre-Checkpoint:  Playing the Field

The first stage of dating is more casually referred to as “hooking up.” (Or, if you’re looser with the goods, “banging.”) If you were shopping for an apartment, this would be akin to couch surfing – staying with various acquaintances as you explore potential future neighborhoods and search for a place of your own. With zero responsibility attached, many find playing Musical Chairs: Sleepover Edition the most fun part of the entire journey, and, perhaps for good reason, never grow out of it. However, the majority of us eventually desire a deeper level of connection, and a more permanent “residence”…

Checkpoint 1:  Going Exclusive

Assuming you haven’t yet decided to return to the open market within the first two or three months of dating (though some stunted commitment-phobes may take as long as six months, often to the chagrin of their blue-in-the-face partner), you might decide to go “exclusive.” Just like subletting an apartment, this is commitment in its most riskless form: you’re dipping the tip in the waters of permanent residency just to see what it feels like. With your own books and furniture still in storage, you can walk out any month you feel like it, without worry of losing a security deposit or (if your partner is particularly vengeful) your balls.

Checkpoint 2:  Pledging Devotion

Somewhere between four to seven months in, you pledge devotion to your partner by uttering those three most equally feared and revered words in the English language: “I love you.” And with that single declaration, you, my friend, have signed your first short-term lease. Perhaps you’ve signed for six months, maybe for a year — but by expressing your true feelings so honestly you’ve now made it clear that you aren’t going anywhere…not for awhile, at least. One brutal caveat to this seemingly lovely Checkpoint: once you make the decision to bare your soul, anticipating your partner’s response can be as torturous as waiting for a sweaty old Slovakian landlord from Craigslist to approve you for a killer East Village apartment.

Checkpoint 3:  Long-Term Commitment

No matter what your relationship is like, everyone experiences the same Checkpoint 3. If you’ve both made it to One Year without shuddering at the thought of continuing to fondle the same genitals in perpetuity, you are now facing the precipice of a long-term relationship. By celebrating your first anniversary, you are, in essence, celebrating the future of your relationship. And while exciting, this can be an especially frightening checkpoint. The decision to renew your annual lease for another year can feel like doubling down simply because, well, it is. And while a lease can always be broken, the undertaking is anything but easy…

Checkpoint 4:  The Co-Op

Whether it’s two, three, four, or ten years after you’ve started dating, eventually you will likely get engaged. Hey, you can only rent for so long, and it’s a buyer’s market. Just as the purchasing of shares in a co-op apartment building forges a contractually permanent housing partnership, a marriage engagement promises a contractually permanent cooperative of love. (Try using this phrasing on your fiancée – she’ll want to elope on the spot.) By the time the contract is signed, the accompanying fear and anxiety of each preceding Checkpoint should be missing from this one. That is, of course, unless you’ve purchased the wrong home. In which case, be afraid. Be very afraid.

I should point out that these days, there is also an exciting moment when real estate and romance intersect quite literally: between Checkpoints 3 and 4 often lies a Checkpoint 3.5, in which a pre-engaged couple decides to move in together. The mingling of personal belongings signifies both parties’ willingness to further intertwine their lives, making separation that much more difficult. Yet, although cohabitation creates complication, it also allows for some pretty sweet rent pro-ration. (Is that a Kanye lyric?)

In reality, timing may vary – these checkpoints are purely emotional, and emerge at their own rate according to the pace of each individual relationship. And of course, I recognize that the blueprint I’ve laid out here reflects a fairly primitive “male” perspective, as it implies eventual “ownership” of the other person. But relationship checkpoints exist for both men and women, and it’s important for couples to acknowledge and discuss them as they come up. If there’s one thing real estate taught me, it’s that open communication with your broker is the only way to ensure your needs as a homeowner are met.

Now go out there and find a nice guy who’s down to get deep into your walk-in closet.