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This Play Sends You On The Most Awkward First Date

The immersive play Red Flags forces you into a first date with a woman who might just hold your hand and ask you to reveal the worst thing you’ve ever done.

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It’s hard to pinpoint the most awkward moment of my date with Emma. It might have been when she showed up late and alarmingly frazzled before immediately demanding a selfie in case I murdered her or we ended up married. Or maybe it was when she held my hand and asked me to pretend we’d already been dating for a couple years, then proceeded to ask me to recount our relationship milestones. I can’t remember the last time a question stumped me quite like a stranger asking, “Where did we first have sex?”

But when I look back on the hour we spent together on a breezy August night in Los Angeles, the moment that makes me cringe the most is when I felt suddenly compelled to kiss her. I didn’t, but I was so startled that the thought even crossed my mind. First of all, I’m gay enough to have never actually kissed a woman romantically. But more pressingly, Emma was an actor and our date wasn’t real. It was a one-on-one immersive theatrical experience called Red Flags. Whatever weird spark I was feeling was pure fiction.

I’m a big fan of immersive theater in theory, but I almost always regret it once some actor is forcing me to don a gladiator outfit or threatening to give me a rectal exam. (These are real things that happened earlier this year, but I digress.) Red Flags was an especially stressful prospect: an interactive show where I was the only audience member. I wouldn’t be able to opt out of participating, or even be confident that the actor would do all the heavy lifting. Plus, there would be no way to make a quick exit if things got weird — and things always get weird.

I was anxious all day leading up to my date with Emma, way more anxious than I’ve ever been about an actual date. (We can think about what that says about me, or we can move on!) We’d had limited contact up to that point: After booking the ticket, I got an email from Emma asking me to fill out “the rest of my dating profile,” which involved sharing my biggest disappointment alongside my favorite dessert. (The latter was a lot harder for me.) The day of, she texted me when and where to meet her, stressing that I should let her know as soon as I got there. “I’m OCD ha ha,” she wrote.

The online communication and the title Red Flags gave me some indication of how this was going to go, so I was prepared for a total disaster. My mind spiraled with all the ways dates can get awkward. I thought perhaps knowing the less-than-desirable outcome would be preferable to the uncertainty that comes with any real-life dating experience, but it wasn't all that comforting. I have a hard enough time witnessing discomfort from a distance; cringe comedies make me want to hide. Here, I’d be an actual participant. In a panic, I came close to canceling.

I’m glad that I didn’t. I wouldn’t call my date with Emma good, but, despite her considerable baggage, I found that I sort of enjoyed her company. And the experience as a whole was illuminating in a way I hadn’t expected.

Emma and I met near a bar in Atwater Village, a cute and relatively low-key neighborhood. She asked if I wanted to get a drink or go for a walk instead. I opted for the latter — walking dates are underrated, as is walking in general in Los Angeles — and we strolled while getting to know each other. She wasn’t holding much back, but then, I’m an oversharer too. I’m also neurotic and Jewish and prone to talking too much about my mother, so none of the obvious “red flags” actually put me off much. I mean, I recognized them, but I tried to imagine how I’d proceed if Emma were a guy I was attracted to. I quickly decided that, against my better judgment, they wouldn’t have stopped me.

It was a bit tricky doing that kind of translation, but I felt like the experience would be most effective if I conceived of it as a real date, and I’m just too gay to do that with a woman. Sure, it took me out of things a bit, but that was always kind of inevitable. The problem I often have with immersive theater is that I can never really get out of my head. I’m not an actor, so I always worry that I’m not properly committing to whatever role I’ve been placed in. And just generally speaking, I tend to be overly insecure and self-conscious, so it’s hard for me to not constantly think, Am I fucking this up? That goes for real dates, too.

But none of that really mattered — and that’s what really impressed me about Red Flags. Because while I was very aware of myself and the fact that I was on a fake date, I also completely bought Emma as a character. That’s a credit to actor Lauren Flans and to writer-director Lauren Ludwig. Emma is a mess, but she’s a mess that I know. At my lowest, she’s a mess that I’ve been. The more she revealed about herself on our date, the more I felt compelled to be there for her. When her fear that everyone hates her kept cropping up — a nagging thought I know all too well — I just wanted to assure her that I didn’t. And yes, when she admitted that she worries she’s bad at kissing but no one will really tell her, I did want to kiss her. (I am a people pleaser; it’s in my nature to reassure.)

Red Flags is not so much about what Emma says as it is how you react — what do you consider to be red flags, and how do you react when you encounter them? Like so much of the best theater I’ve seen, Red Flags forced me to dig deep and be introspective in a way that was sometimes deeply uncomfortable. I came away from the play feeling like I’m agreeable to a fault, willing to give everyone too many chances out of a dangerous blend of compassion and guilt. Even when Emma revealed her darkest secret, the one that should send every sane person running for the hills, I gave her a hug and felt genuine concern when she abruptly bolted. I knew she wasn’t a real person; I just really wanted her to be OK!

I would never try to convince someone to attend Red Flags (and you might not even be able to because it’s currently sold out) — immersive theater is not for everyone, and the forced intimacy of a one-on-one show like this is especially confronting. But I’m glad I stepped outside of my comfort zone, because I do believe that theater should challenge you, whether that means forcing you to think more seriously about why you’re single or briefly making you question your sexuality. Sometimes it’s good to feel unsettled.

As I was walking away, I got a final text from Emma with the selfie she’d taken of us. I squirmed when I saw it; I look about as awkward as I’d felt. “I know we’re not getting married but here’s this picture anyway,” she texted. “Thanks again for a fun time.” I didn’t want to leave her text unanswered, so I replied, “You never know. Thanks, Emma.”

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