(left to right) Amanda Drinkall, Alex Weisman and Tiffany Oglesby. Photo by Michael Brosilow.

By Catey Sullivan

We’ve all been there: After hours of torturous emotional labor, you’ve finally captured just the right tone of nonchalant coolness in a pithy, witty email asking your crush out for a totes cas’ drink, and right after you hit “send” you happen to catch a glimpse of yourself in the mirror and you realize the visible belly outline under your shirt is freaking ginormous and, who are you kidding, you look like a beached whale, and you are the most disgustingly unattractive person on the planet and nobody in their right mind would want to have even a casual drink with you, much less date you and obviously nobody will ever love you, you’re going to die alone, or at best surrounded by cats, and in either case, you’re an abject failure and always have been and will be and you’d basically kill your own mother to get that email back but you can’t so now you’re going to perish in a state of pathetic mortification as well as utter aloneness.

So it goes for Jordan Berman, the 29-year-old gay man at the cracked heart of “Significant Other.” Mimicking life itself, playwright Joshua Harmon’s drama vacillates between raunchy rom-com and poignant tragedy. The piece feels unfinished and at times a bit unfocused, but it’s anchored by a wrenching, funny and compulsively watchable performance by Alex Weisman. Directed by Kiera Fromm, “Significant Other” also boasts a wonderfully compelling supporting cast. It’s a flawed script, but a winning effort.

At the center is the intensely needy Jordan, closely orbited by his three ride-or-dies. Jordan, Laura (Amanda Drinkall), Kiki (Cassidy Slaughter-Mason) and Vanessa (Tiffany Oglesby) were best friends from college, and remain a watertight crew years out. Or so they do until Kiki gets married.. And then Vanessa gets married. And finally, Laura gets married, which sends Jordan into a spiral of self-loathing, insecurity and deep-seated panic.

His unraveling is both painful to watch and, at times, hilarious. The loss Jordan feels as his anchor relationships pull up and leave him adrift is excruciating, and in Weisman’s performance, rendered with tearful authenticity. But he’s also someone you can’t help laughing at (and sometimes with) because he’s so over-the-top and so insecure.

If you’re looking for a story about a gay man who is strong, autonomous and not periodically filled with self-loathing, look elsewhere. Jordan is hyper-articulate and just as needy. The word “obsess” comes up a lot with him, usually in the context of wanting to find a significant other for himself. At times, Jordan’s insecurities border on “Crazy Ex-Girlfriend” levels of OCD and mental illness. Purchasing a pair of size 12 forest green Converse high-tops for the sole purpose being able to wake up next to the the exact same shoes that the dreamy guy in the office wears? That’s weird. Realizing you’ve just lost five hours Facebook stalking the guy you crushed on in high school? Surely we’ve all been there to one degree or another.

Harmon has a knack for pithy dialogue that cuts to the heart of complex issues with brevity and depth. “Life is supposed to be this big, complicated thing,” Jordan says at one point, “But actually, it’s pretty simple. Find someone to go through it with.” The hard part, Jordan adds, “walking around knowing what the point is and not being able to get it.”

Then there’s the rather ominous advice his beloved and exasperating grandmother (Ann Whitney) gives him: “Don’t get old. Don’t die young. But don’t get old.” Outliving all your friends and your purpose? Trust, says grandma. That’s something to avoid.

And finally, there’s Jordan’s concise lesson in anatomy and erections. The latter, he notes, happens when the heart pumps an engorgement of blood downward. “Anything that has to do with your dick has to do with your heart,” he concludes.

Jordan’s story is messy and unfinished, and while that’s accurate reflection of real life, it also leaves “Significant Other” feeling like Harmon abruptly ran out of ideas decided to simply call for a blackout and call it a day. What makes it work is Fromm’s cast.

Weisman’s Jordan is relatable, no matter where you are on the sexual orientation or neediness scale. Weisman has always been superb at capturing vulnerability, but there’s far more to Jordan than raw insecurity and want. Jordan has a ferociously demanding monologue during Laura’s bachelorette party. It’s an anger-and-fear fueled passage that captures all the frustration and rage that can pile up when you’ve been intimately involved with serial weddings, none of them your own. The crazy expense and time commitment, the terror that comes from watching everybody you love pair off without you, the way crazy-happy newlyweds can put your own miseries into sharp relief – Weisman articulates them all ruthless honesty.

Jordan’s friends are also memorable. Slaughter-Mason is terrifically funny as the vain, shallow (but fun-shallow) Kiki. She’s borderline obnoxious, and will probably be both a terrible mother and a divorce before she hits her mid-30s, but she’s also a walking party and you can see why her friends stick with her. As Vanessa, Oglesby is acerbic with just enough genuine warmth to keep the character from becoming a one-note cynic. As Laura, Drinkall is the sunny, compassionate sweetheart of the group.

Whitney is excellent as Jordan’s filter-free, slightly dotty grandmother, offering up advice that initially sounds innocuous enough, but becomes more disturbing the more you think on it. As the unattainable Adonis Jordan pines for, Benjamin Sprunger is appropriately taciturn and God-like.

That leaves Ninos Babos, who is stuck playing a gratingly stereotypical role that’s so limp-wristedly over the top the play would be better off without it.

That aside, “Significant Other” is entertaining. Although if you’re 29, single and deeply worried about being single? Stand forewarned. It might hit close to home.