I Saw The Signs So I Asked Him Out Via Email

I’m sorry if you were expecting a wonderful, epic love story of how I used old school correspondence to get the guy of my dreams in the Modern Love kind of way, which is probably how a majority of you found yourselves here. Unfortunately, there is no romantic story. But there is a romantic lesson and that’s why I’m writing this.

I’ve spent the last 3 years of singlehood shaping myself into the modern woman I’ve envisioned for myself—to be the girl of my own dreams. I own credit cards. I pay my bills on time. I work 9 to 5 Monday through Friday, and balance three other side gigs. I rent an apartment. I take the subway. I read plenty of books. I work out. I cook for myself. I enjoy New York nightlife and social scenes, sometimes even by myself, as any twenty-something thriving city girl should. In my mind, I am fulfilling all the checkboxes of a woman doing her own thing without concerning herself with the societal norms of what a woman ought to be. And in the process of doing so, the right things, opportunities, people, men will come along. Just focus on yourself, I’d tell myself. The rest will fall into place as they should and as you manifest it, I’d reassure myself. So manifest I did by inking a mental checklist of peak moments I believed made me more fiercely and independently woman. 

One night, I was talking to a fellow single girlfriend about our struggling dating lives and she mentioned that she asked guys out plenty of times before because she was tired of waiting for them to make the move, to which I promptly and too enthusiastically replied, “Wait, you’ve asked guys out? That’s amazing and I completely respect that! I need to do that more.” I remember thinking to myself, But why haven’t I done it yet? This mental checklist of mine, so unending and extensive with things like, Travel somewhere solo. Start my own business. Write a book. Speak at Ted Talk. Surely, how could I miss something as simple as asking a guy out? And I most certainly did not want to be the woman who never asked a guy out in her life, not the kind of woman I’ve directed myself into becoming, anyways. I mean, all the great women I’ve met or looked up to have done so sometime in their lives. Even female-led brands like Bumble and The Wing are built upon the foundational idea that women can and will take charge. Modern day women are out there paving the way for the rest of us, and yet, I have already gone over a quarter of my life without having asked a guy out. And so from that sheer eye-opening epiphany, I firmly decided and promised myself to cross it off soon. Ask a guy out, damnit. You fierce, independent, modern-day woman. 

It was like a glaring sign from the universe. Just weeks after this mentally etched promise to myself, the perfect opportunity came along. I was volunteering at a music gig as the MC of the night out in Bushwick, having crossed two bodies of water from Jersey, and on a weekend nonetheless. I wasn’t initially scheduled for this show, in fact, it was a last minute fill-in that I had decided I could step in for, which is particularly rare for me because on top of the tedious commute, I almost always have other preferred commitments on Saturday nights (I’m a socially ravenous extroverted millennial, okay?). But on this particular Saturday evening, my plans were wide open and I figured, sure, why not? Basking in the beautiful summer evening on my way there, I stopped by an outdoor sale by a man who laid out all his treasures to sell for whatever price people wanted. A quick glance and I found a copy of a book I’ve been meaning to read amidst the vast spread of nicknacks. For a mere $5, he sold me the book and told me he just wanted people to give trash a second chance. How wholesome and lovely, I thought, under the golden hour glow. The nuanced details piling up to become a night already prefaced by charming chances from the beginning, unexpected events happily working in my favor, so it only seemed fitting that the rest of night unfolded according to theme as well. I entered the venue (after walking passed it three times) and there he was. Undeniably tall and fairly handsome, but not arrestingly so, and unassuming in his polite manners. Other than his noticeably good looks, I don’t even remember what my first thought was, which is uncharacteristic of me because normally in the presence of seemingly handsome men, I’d internally freak out and text all my friends to express my fangirl moment as I summoned all efforts to maintain a collective coolness. But in this moment, I only wanted to do my job and enjoy a night of music and good company ahead because I was enjoying this time for and by myself, and no guy was going to take that away from me no matter how good looking. Very good looking. 

I focused on running the show as usual—meeting the hosts, chatting with the artists, getting to know the other volunteers, setting up the place. Moving steadfast and determined as if declaring that I was in my rightful element and nothing was going to stop me, but also hoping I’d exude a semblance of womanly confidence because this girl in a vibrant maxi skirt contrasted with beat up Converses is a girl who knows who she is. Until said handsome guy came up to said girl and opened up a conversation that immediately established plenty of common ground, the dialogue animated but with genuine enthusiasm, and loads of interminable banter. You’re a whiskey neat person too? Wait, I didn’t know anyone else who listens to that podcast also! Those are definitely my top three Kanye albums! You should look up this artist, I think you’d like him since we seem to have the same music tastes. And on and on it went. Oh no, I thought. I was doing so well keeping to myself. But it was so natural and easy, and I always thought that’s how it should be—free of small talk and forced conversation that usually gave way to my nervousness and awkwardness. How could I not perceive this as a sign of fateful opportunity designed for my unequivocal redress? After all, they say you meet someone when you least expect it, and surely, the night had proven to be remiss of expectants.

Once the show ended, we were the only volunteers left after cleaning up. I took my time saying thanks to all the artists and hosts, I was on a socializing high and feeling pretty damn good about myself. He was nearby waiting for me, or at least it looked like it as he was doing that thing we all do when we don’t want to look awkward idly standing there so we frequently check our phones. And I’m not sure why since he could have left a while ago but as I said, he was polite and quite honestly, it just felt nice to be waited on. We walked out together, resuming our conversation from before, casually pacing side by side. I don’t want this to end, I thought, as we were approached a corner and knew we’d be parting ways soon. This is it, Mai, now’s your chance to ask him out. All these clear signs from the universe signaling to you that you have all the evidence you need to make the move, and it would be a terrible waste of fate not to act upon it. We hugged our goodbyes and hoped to see each other at the next show. And as we separated, lingering towards opposite directions, I called out to him, And maybe we can get drinks sometime? Possibly some good, old-fashioned, whiskeys? Smooth and simple, good work, I affirmed silently. To which he coolly, oh so charmingly, replied, I’d love that. I’m always down for a good whiskey.

Like a little middle school girl, I commuted home giddily and rousingly afloat from having performed such a glorious quake of a gesture in my otherwise tideless life. I wanted to hold onto this feeling all to myself for a while longer, not telling anyone until I got home because it felt like a dream that would immediately dissolve at a word’s notice. Did I really just do something for myself? Did I really take charge of my own love life? Did I just ask a really good-looking guy out on my own and he actually didn’t reject me? All these thoughts racing on and on, and while I’m usually careful not to quickly free fall into my romantic cliches as I tend to do, this time, I happily let my mind run wild with the whirlwind of possibilities. Not in the clouds but on the ground, right here in my own actual reality. 

I pulled up my email to get the contact list of the volunteers that night, and as I scanned for his name, I came to my first crack of disappointment: he had his email but not his phone number. Are you kidding me? My number was happily perched right above, yet all he had was an email. How conveniently ironic, my life continuously playing cruel jokes on me and I couldn’t even glean anger because somewhere in the back of my mind, amidst this exhilarating, magical day of pleasant chances, I knew my life was not built on such pleasantries without a harsh reminder from reality. You couldn’t have had it that easy, Mai, I told myself. Some things are only meant to be for that moment, and that’s it. Don’t be a fool.

Except, I refused to let that be it. I refused to let my life dictate how things have to be just because they always were that way and simply settled for my disappointments as so. I refused to let my grand gesture—not just in asking a guy out but also in making something happen for myself because I wanted it to—slip into the abyss of could-have-beens, dusted with humiliation. There was a strikingly new sensation that overtook me now advocating that I will not let my actions exit quietly anymore because if they’re going to leave, they’ll leave with dignity and meaning. Do you ever have those self-justice moments? Times when you aren’t spilling your life into fate’s hands but actually grabbing it and holding it for yourself? I wasn’t going to invalidate that feeling because I’ve learned that life isn’t just wrapped up presents of moments to be shelved. Life—my new life that is—is about making things last through their underlying purpose. My life will be collection of open-ended and reopened gifts to myself, when I choose them to be. 

So I emailed him. And asked him out again. My ironic life once again being ironic because for someone who swore off dating apps, here I was emailing a guy. Nonetheless, I felt mighty and proud of my 200-word write-up that took about three drafts and two extra sets of eyes for approval, sprinkled with the right amount of nonchalant wittiness and charming personality.

It was a full week before I heard back, which usually isn’t a good sign because if he had felt the same energy as I had that night, he would’ve jumped on responding immediately. Ugh, he’s one of those assholes. So inconsiderate and subsumed with male righteousness. But alas, he did reply, apologized for the delay, and wrote more than two words, actually wrote subsequent paragraphs, and was overall well-meaning. All good signs, hopeful signs, until the end of the email. I just want to let you know that I have a girlfriend. I read it once more. I apologize if I was/came off presumptuous. Of course he did because didn’t I mention that my life is imposed with ironies. Why would the fact that I misread all the signs, after double and triple checking that they were indeed positive signs, be any different? 

It's easy to think all guys are assholes—that he was too self-absorbed and deep in his male ego that he entertained himself with the idea of a girl flirting with him to get his attention. It would’ve been easy to to tell myself he was “one of those guys”. But as they say, it really be like that sometimes. More thoroughly, some things are just as direct and simple as they present themselves. And born from this waking realization (thanks to millennial slang), I concluded that this event was nothing more than a nice guy making conversation with a girl who enjoyed the natural ease of it all. Of course, it was more devastating than the definitive, hard rejection because there was nothing to be done about it. It wasn’t anyone’s fault, it wasn’t my fault, I’d tell myself several times over the course of the week. It’s easy to think it’s you—that you were wrong or did something wrong or made the wrong move or said the wrong thing. It’s easy to think this was karma for that time you ghosted the Bumble guy who took you out on the most perfect first date. But the biggest revelation is that, it was only a grand gesture in my mind because I let it be (I can’t help that I am a cheesy hopeless romantic). He was the idea of the guy I thought I deserved and the universe presented me with a challenge to overcome because after all, what better way to prove my growth if not put it to the test?

Here’s the other thing, regardless of the dead end, I did it. I asked a guy out and that was my goal. Not that I was supposed to ask the guy out and he’d say yes but that I did something for myself and still honored my growth through to the end. Perhaps all the signs I perceived were actually telling me that I’m finally manifesting the kind of life and the woman I want to be for my damn self. And maybe that’s the kind of modern love I need right now.

There are so many learnings to be acknowledged from this entire experience, and as I reflect now months later, I realize this is the best first rejection I could have asked for. I look back and can’t help but smile at how perfectly imperfect it all was. Sure, it would’ve been nice to have ended it with a “And now, we’re in a happy, loving relationship all because I was bold enough to ask over email.” But I think what makes this narrative less majestic but admirably realistic was that I saw a side of me I didn’t know had within me. I took the initiative in being triumphantly chivalrous for myself and for that meek little girl I used to be. I took the initiative in listening to my feelings and even the feelings after that transpired from the rejection and came out braver. I won’t deny that it's made me more jaded but it has also given me new resilience and become less fearful of doubts. I am that woman now, the kind that asked a guy out on email and ultimately, didn’t crumble in embarrassment. So if it means awakening new capabilities stirring inside me that deserve an opening, I’m ready for more rejections. After all, why let the guys have all the fun.