The Dating Coach
When Harry Met Allie
Not every meaningful connection results in love
By Allie Roodman December 5, 2023
Per my date’s instructions, I offer his name, Harry. “Yeah hi, can you put my car under Mr. Smith?”
“Mr. Smith? Of course!” The young valet at the Four Seasons is suddenly more friendly. “You must be Ms. Roodman,” he says as he eagerly takes my keys.
I walk across the lobby toward the restaurant maitre’d, squeezing my abdominal muscles to balance in my heels on the marble floors. I identify my date from his photos sitting at a table in the back corner. To the chagrin of friends and family, I recently reset my dating app age preferences to max out at 45, not 40.
Mr. Smith is 42. I am 31. He’s wrapping up a business meeting, I can tell by the way he introduces me to his colleague, who promptly excuses himself and leaves our table. Mr. Smith is sitting laid back in a club chair with one leg crossed over the other. I sit upright with perfect posture.
“So, Allie, what’s up?” he says without looking up from his phone. He removes his Tom Ford glasses and cleans them on his Faconnable sweater. I notice the monogram on his sleeve.
“Not much, how’s your day going?” I ask. Mr. Smith looks up from his phone only to catch the attention of the waiter, ignoring my question. He orders another drink, and instructs me to do the same. Initially thinking I’d have wine tonight, I opt for an old fashioned. I need something stronger.
“You know, you’re better looking in person,” he says, still without looking up from his phone. “You should change the photos on your profile.”
I’m a bit taken aback by his comment, but decide to be polite. “Thank you, I’ll think about that.” He then proceeds to tell me his life story, unsolicited. As he speaks, I can tell he’s given this speech at least a dozen times before, and I begin to understand what I am to him, just his 7 o’clock date. Maybe his third of the week, or even his third of the day. I wouldn’t be surprised if another young woman rolled up at 8 p.m. sharp.
Nothing he shares feels out of character with his dating profile. Stanford undergrad, Harvard Kennedy School. He initially thought he wanted to go into politics, and with his humble background, could actually go far, or so he tells me.
Now, he works in finance, at Goldman Sachs. The company brought him out to Seattle lead his division from the New York office.
As I listen, I nod along to show interest. He’s pretentious, sure. But that doesn’t bother me. It’s his complete disinterest in me, although if I’m being honest with myself, I could have predicted this. True to form, when it’s my turn to talk, he cuts me off, again, to ask if I like his jacket. “It’s O.K.,” I offer.
“Just O.K.?” he laughs, amused by my review. “It’s Russell Wilson’s brand. I’m on the board.”
My old fashioned arrives and I take a big sip to wash down my annoyance. He likes power, control. I no longer care to play nice. I’m over it. “Did you just bring up your jacket so you could tell me you’re friends with Russell Wilson?” He pauses and starts to laugh a bit. I relax into my chair.
“What no, of course not.” “Ya, right.” It’s my turn to cut him off. I spot a cherry at the bottom of my drink, and proceed to dig for it with my spoon, basically signaling, “you’re no longer interesting to me.” I have his full attention now, though I’m not sure I want it. “You’re cool,” he finally says.
“Thank you,” I say through gritted teeth, which are busy chewing on my cherry stem. Now that we’ve arrived at a truce, he begins to open up. He talks about his recent divorce, and I find myself drawn in by his vulnerability. He’s actually pretty likable when he isn’t being a big shot.
The evening ends on a good note. There’s no romantic interest whatsoever, but at least there’s respect. As we leave, every staff member we pass says goodbye and addresses him by name.
Not five minutes after I pull away from the hotel, my phone rings. It’s Harry.
“I just want to say I think you’re incredible. And I was wondering if you were doing anything tomorrow night?” The compliment is ridiculous, but he must’ve realized he was being a dick. Intrigued by his new strategy, I tell him I’m free and we make plans to meet up the next night. Why not?
The next night we meet at the Roanoke, a popular and historic yet somewhat divey bar on Mercer Island. I thank him for offering to come to me. I arrive first, and sit at a booth near the front. It’s crowded, and I’m relieved I don’t recognize anyone.
He enters and sits across from me. “So, these are your stomping grounds,” he laughs as he takes a look around. He’s more casual tonight, trading in his loafers for Veja’s, but he still pairs them with a Ralph Lauren cardigan. It’s not often I go out with a man who’s better dressed than me. The evening is more lighthearted. I enjoy myself. It feels comfortable, and he seems like a different person from the guy I met last night.
The third time we hang out, he confides he’s still hung-up on his ex-girlfriend, a 21-year-old German model he met at Coachella. The cliché would be funny if he wasn’t genuinely heartbroken. He adds that most guys wouldn’t divulge that information, but he’s a good guy, and he wants to do the right thing. I make fun of him for doing the bare minimum. Given the circumstances, he asks if we can just be friends. I agree that’s probably for the best. He gives me a kiss on the cheek goodnight, and says we’ll talk soon.
Over the next few weeks, Harry and I regularly get together for drinks to discuss our dating lives. Despite the snarkiness between us, I get a kick out of calling out a grown man on his antics. For instance, he claims to want to find love again, but dates 20-something-year-old models in New York and Los Angeles. “Harry, no offense, but you think they’re not into you for your money?”
He also forces me to face facts. I recently started hanging out with someone I saved as “Hot Guy” in my phone. I beg Harry to tell me I have a shot. “He’s got you Allie. He knows you care. He’s not into you.” Not what I want to hear, but I appreciate his candor.
This story happened slightly more than a year ago. In the beginning of our friendship, things were a bit rocky at times. But for whatever reason, we both continued to keep the relationship alive. Since last winter, Harry has become one of my dearest, closest friends, and he views me the same way. Through pure coincidence, we met each other at our lowest points, and I like to think we helped each other “get back on track.” We keep each other in check, and value each other’s opinions.
Most importantly, we trust each other. I value him for his intelligence, and insight into the male brain. Our friendship is a bit unconventional, but it’s mutually beneficial. There’s mutual respect, admiration, trust, and loyalty. We support each other, have met each other’s friends, and will always take each other’s calls. We have fun together and have a natural banter. And yet, it doesn’t quite add up. At different points, I think we’ve both contemplated trying on something more than friendship.
On one phone call, he asked if I thought we would ever work. “I think there’s love here,” I answered, “but I don’t think it’s that kind of love.” He agreed. From dating, I’ve learned that a connection doesn’t always equate to a relationship. You can have a connection and arguably be compatible, and it doesn’t always mean a romantic relationship makes sense. It’s a hard pill to swallow sometimes because it feels like finding a real connection can be hard to come by. There’ve been times where I’ve thought, dang, wouldn’t it be so convenient if it was Harry? And yet, you can’t force it. Even if you don’t find the person, you can still make a friend.
I’m grateful to have Harry in my life. I love him. But we’ll always be just friends.
About the Dating Coach Column
Allie Roodman is a 31-year-old millennial trying to navigate the modern dating landscape, one bad date at a time. She uses her own experiences to help others find love in her day job as a matchmaker. She is figuring it out as she goes, just like the rest of us. Connect with her on Instagram: @allieroo