Location, Location, Location! The following month, I woke up to an email from Claire, a vibrant photographer I’d been working with on and off for the past few years. Lauren and I had set her up with her previous boyfriend, but when things didn’t work out with them, she’d resurfaced, wondering whether we had anyone else in mind for her. I told her about Jim, a self-assured and athletic talent agent, hoping they’d hit it off. According to her feedback after the date, she found him “cute and easy to talk to,” but she had objections. “Sure, he’s successful,” she wrote, “but he was ten minutes late, talked a little too much about his achievements, and was a bit of a name-dropper, so that hinted he could be a little immature or ego driven. He had also just recovered from a Ritalin-fueled fifty-hour work streak. All in all, decent conversationalist, bad lifestyle fit.” Oh, Jim. I sighed, annoyed—at Jim for not getting his act together, and at Claire for not seeing their potential in spite of it. But, more than anything, I was annoyed at myself for sending them to Petty Cash Taqueria. Despite its convenient location and rightful title as one of LA’s “mezcal hot spots,” the restaurant had barely produced any second dates between my clients. I vowed to stop sending people there, a promise I’d forgotten with everything else I’d been juggling lately. I silently r eprimanded myself for the error. After all, I’d taken the time to sort through years of previous date statistics in volving my clients—out of sheer curiosity and perhaps too much time on my hands—and knew offhand which restaurants were most likely to yield second dates for singles, and which ones likely interfered with that process. After recognizing some undeniable patterns, I started taking clients’ feedback on date settings as seriously as their chemistry with their matches. What kind of service, food, or ambiance is most effective for finding love? After a while, the data seemed to speak for itself. For starters, great parking. If someone spends twenty minutes searching for a spot, or begrudgingly dishes out for overpriced valet, their energy coming into the date is more likely to be negative. Petty Cash happened to be located on a busy street where finding good parking was tricky. Viviane at the Avalon Hotel, however, was less trendy, but offered free valet for anyone dining at their establishment. I suspected that the bachelors I sent there for drinks regularly left with firm plans to see their dates again in large part due to the convenience and ease of the parking experience without the added price tag. I’ve also found that privacy, but not too much of it, matters. Petty Cash featured communal tables: great for people-watching and striking up conversation with strangers, but less conducive to creating a rapport with one person. (I hate dates when couples sit at bars for this reason. Some people believe the casualness of the bar seats will be disarming for their matches, but the close proximity to others can backfire. Instead of focusing on their date’s wit, charisma, or kindness, people can be so preoccupied by who might be watching or eavesdropping that they aren’t present for the conversation.) When booking reservations, you should consider an actual table where outside influences aren’t a factor. If a table is too private, though, awkward silences are more apparent, and diners lose the ability to gossip about those around them—a vital crutch when a conversation stalls (e. g., Are those people one table over on a date too or having drinks with a coworker? Is that woman in the corner waiting for her date to show up? Or is she an escort?). The noise factor is also a consideration. Whether a spot is blasting a cool, rock-inspired soundtrack (Petty Cash was named after Tom Petty and Johnny Cash, respectively, so the music was always top-notch) or
bustling with activity, a balance needs to exist between hearing your date and feeling like you’re at a happening location. Airflow is also commonly overlooked. Even outside a health context, I find that airflow has become a measurable part of someone’s comfort level and prompts a whole new set of questions: Is a patio there? Are you comfortable? How’s the view? When the weather’s nice, I often schedule first dates at rooftop locations to take all of those concerns off the table. I’ve also learned that regardless of how desirable a venue might be, switching it up is important. In my early years of arranging dates, I’d send clients to the first places that would populate my Open Table or Resy accounts, not tracking whether a client had been there before. It might have been an innocent inconvenience the first few times, creating a sense of an unpleasant routine, but it d eprived them and their new date of the joy of experiencing something new together. (I have select clients who thrive in familiar settings, so for them, I tend to rotate among the same three or four places.) I started to consider all of it, and spiral more about Jim and Claire—whose date didn’t even sound that bad. Was their poor connection really a result of my restaurant choice (it pained me I would never know), or had they been a doomed match from the start? I’d been certain the two would have instant chemistry or, at the very least, enough interest to make it to date two. Aside from being each other’s ideal physical type, I thought Claire would find Jim charming and intelligent, and that her even-keeled temperament would balance him out well. He was edgier than the men she normally dated, but successful and grounded (at least when he got enough sle ep). As I closed Claire’s email, I wondered if either of them had at least enjoyed the restaurant’s highly acclaimed aguachile. As I entered my office after lunch, I was hoping Callie could help turn my day around, which was a lot to ask from a client who had yet to give me a win. We were meeting shortly to discuss her date with Ethan, a promising VFX company owner and database member I set her up with. During her re cap, she claimed to be “unexpectedly attracted to his long hair and painted black nails,” and loved that his teddy bear personality “didn’t quite match his more punk appearance.” She also said she appreciated his emotional and financial stability, and the fact that he seemed ready to have kids. But she’d already told him she wasn’t interested in another date, and I couldn’t imagine why. “He’s from the same hometown as my ex,” she revealed in the opening moments of our session, as if that was an obvious disqualifier. “Where’s that?” I couldn’t remember off the top of my head, and pictured some sort of small-town rivalry between Ethan and one of Callie’s ex-boyfriends, stemming from dating the same bachelorette from a neighboring Midwest farm in high school or something. “Miami,” she r eplied coolly. My head nearly exploded. “Wait, you won’t go out with him again because he’s from Miami? Am I supposed to rule out anyone who happens to be from the Greater Miami area?” I posed the question slowly, in case she was forgetting the nearly half million people who live there. “Well, not necessarily,” she attempted to backtrack, but I could already tell the answer was yes. Carefully and calmly, I looked for opportunities to ask more about her dating history, hoping to receive clues about her avoidant behavior. Before long, I learned more about her most serious ex, whom she broke up with over children. Both had wanted them, but he preferred to wait a few more years, once he was more established professionally. Callie had wanted to try conceiving within one year of meeting him, and a few years felt too long to wait. She told me this was four years ago, without acknowledging the mathematical irony. “He’s married now with a kid. But you know what?” She conjectured, “If he was meant for me, my timeline would have worked for him.” The confidence with which she said it surprised me. It’s not often that you hear someone deliver such a clear opinion on something so ambiguous. But
then, I realized: she came to that conclusion because she had to. The alternative —that she’d messed up, and might have wound up with a great guy had she only been more patient with him—might have been too much for her to acc ept. Timing is a huge point of contention in the dating community. Some people believe that it matters on a near-cosmic level. Others think it’s just what you make of it. “Boo Boo would have been right for me whether we met now or when we were kids,” my best friend used to insist about her now ex-husband. I, however, couldn’t be more certain that Dave and I would have butted heads when we were younger. I’d have labeled him a “stoner hippie,” and he’d have called me a “giant nerd,” a designation he now uses as a term of endearment. We’d since had the same conversations as Callie and her ex about what our respective timelines looked like in terms of children and other major milestones, and for us, the topics had been tough to navigate. After we got married, Dave wanted to start trying for kids immediately. Being younger than him, I felt less pressure and, like Callie’s ex, wanted more time to grow my career before launching into yet another life phase. We had gotten engaged after only ten months, and there was so much more I wanted us to do together before taking on additional responsibilities, like attend a music festival or visit Australia. Dave implored me to reconsider: he really didn’t want to be an “old dad.” He was in his early forties, and in his mind, prone to imagining worstcase scenarios, he was going to die before our kid graduated high school. Truthfully, I didn’t want Dave to be an “old dad” either. Being the only one of us with enough energy to chase around a toddler wasn’t exactly an appealing scenario for me. Through our wonderful therapist, Dr. Christopher Walling, Dave and I came to realize that there was no such thing as a “his” and “hers” timeline—at least not in a healthy relationship. While I came into ours with preconceived notions about when I wanted to have kids, Dave was the partner I wanted to have them with, and with that came certain realities such as his age. By considering us as a unit, rather than myself as an individual, I discovered his timeline was actually ours. (And it’s a good thing we started when we did, given our need for fertility assistance.) Now that Callie was older, her desire to have kids was playing a larger role in her dating life, but it was leading to its own form of self-sabotage—her negative and intense energy counteracting her end goal of making a lasting romantic connection. Rather than explore her potential with a match organically, she was making dates feel more like interviews, and alienating potential life partners, and baby daddies, as a result. When I’d asked Ethan his thoughts on Callie, he r eplied that she was attractive and interesting, but also intense. “She asked about my medical history, eating habits, and timeline,” he told me in confidence. “I felt like she was more interested in my sperm than me.” I felt for Callie. I understood why she was interested in this information, but could also see how, for Ethan—and most matches simply looking for a relaxed, light conversation on date one—it might have felt uncomfortable. While I’m typically annoyed when men “request” younger women for their setups, for every guy who does so, there’s typically a jaded woman in a rush who once turned him off from other women her age. “Tell me about your parents,” I pivoted. “I don’t talk to my dad.” Callie shrugged, as if this were no big deal. “My parents had a great marriage, or at least I thought they did. Until he fucked the intern. Don’t worry, though,” she reassured me quickly. “I’ve covered this plenty already in therapy.” I smiled to indicate I wasn’t worried at all. In fact, her disclosure had offered more clarity than I’d gotten at any point in the process so far. That she was having trouble allowing romantic prospects to get close to her after watching her own parents’ marriage fall apart made sense now. The most important male figure in her life had revealed himself to be untrustworthy in a relationship. Carefully, I asked whether she could picture herself having a more successful partnership than
her parents had, and she struggled to answer. “Allowing your mind to go there’s important,” I encouraged. “I’d give different advice if you didn’t truly want to be loved the way you deserve, or if you really believe that it’s not in the cards for you. But I don’t think you’d be here if any of that were true.” I gave her a moment to process that somewhat complicated truth. “I want to introduce you to someone amazing, the kind of person I know you dream about. But you can’t just say you want that. You have to take the st eps necessary to make it happen—and that means giving people a chance, even if they’re from Miami. Or wear way too much hair gel.” “Or don’t use social media,” she added playfully. “But seriously, who doesn’t have an Instagram account these days?” I breathed a sigh of relief. The Callie I first met was back. “I don’t know... serial killers, loners, Jennifer Lawrence, and some busy CEOs?” I responded cheekily. “Jennifer Lawrence doesn’t use socials?” Callie looked incredulous. “I don’t think so. But see how quickly a possible red flag turned into a beige one?” I asked. This felt like a good place to wrap up our session. We’d gotten into some pretty heavy subject matter, and I was glad that things were ending on a more lighthearted note. Before we parted, Callie admitted that although it didn’t work out with Ethan, higher-quality men and women had been messaging her on dating apps ever since we tweaked her profile. “All that’s left to do is r eply to them,” she said hopefully. And for a moment, I believed her.