(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.