I recently received my first unsolicited photo from a potential online suitor—a photo of an orca whale. Some backstory: I was staring down the cool barrel of 30, and despite fervent protestations that I was happy alone and not in the market for a husband (or even a casual boyfriend), I’d just succumbed to gentle suggestions from friends and family that I might at least open myself up to the possibility of meeting that elusive Special Someone. Well, fine.

I dutifully filled out my newly minted OkCupid and Tinder accounts. I chose OkC because a good buddy of mine had found himself an awesome girlfriend on the site and Tinder because, well, duh.

More important, both are free and seem less serious than pay-to-play sites like Match (largely for marriage-minded daters) or eHarmony (largely for Jesus-minded daters, I think). And those are just the “mainstream” sites. If I were the rustic type, I might try FarmersOnly. If I didn’t love bread so much, GlutenFreeSingles.

Like many people, I got a thrill out of the easy Tinder game of swiping left for “no thanks” or right for “well, maybe” depending purely on how doable a guy looked. After a lot of left swiping, I matched with a man who seemed promising. He hit all my checkboxes. Dark-haired and slightly dangerous-looking? Check. Covered in tattoos? Check, check! He claimed to “represent a couple artists in the music industry,” and his photos painted him as a dude who liked to drink beer, owned a motorcycle and had a general disregard for the Establishment. Basically, the kind of guy Mom would rather you didn’t bring home.

We exchanged a flurry of Tinder messages, mostly about our favorite bands, and it was going well enough that I handed over my number so we could set up a time to meet IRL. That’s when things got weird. Casual pressure for sexts (“nip pics”—ew) turned to anger, and after declaring that we “were done here,” he sent me the fateful whale photo, with the text “this is your selfie.” As baffled as I was by this rather clumsy attempt at a fat joke (did he have that photo saved on his phone, just for moments like this?), I was more confused by how quickly the whole encounter had gone south. I stopped using Tinder soon after.

But I was curious. As the city’s ONEin3 initiative notes, Boston is home to the largest proportion of young adults of any major U.S. city, and 82 percent of those 20- to 34-year-olds are still unmarried, no less. So why was it so hard to meet a not-creepy person to have a beer with in this town? Perhaps if I changed my methods, it might alter the madness? So I embarked on a quest to try a number of different Boston dating apps and services, to see what else was out there.

First up was Who’s That, a group-dating app created by BU grad Sam Davidson and BC alum Brian Sachetta. Who’s That takes some cues from the popular New York-based startup Grouper. You sign up with a couple of single friends, upload some flattering pictures and go fishing for another group to meet for a date. The idea is that meeting up en masse takes off some of the pressure, and the app attempts to address the pitfalls of nearly blind dates by pulling information from Facebook, so you can see who and what you have in common.

I downloaded the app, which was fairly easy to navigate if not very sophisticated, and coerced a couple of single friends into joining the experiment. There was only one problem: The median age of the guys on Who’s That appeared to be around 22. I was hard-pressed to imagine what group of baby-faced early 20-somethings would have a whole lot of interest in meeting some 30-year-old ladies for drinks. Why, thank you, sonny, I would love a shot of Metamucil with my cocktail. If you’re lucky maybe I’ll take you for a ride on my Rascal later, if you know what I mean.

Another problem was that there didn’t seem to be many people using the app yet. It launched quietly just this past spring, and until mid-July it was only open to current college students—kind of like Facebook, until all the old folks joined and ruined it. I’d scroll through the same groups of Sox-hat-wearing youngsters, clutching cans of Bud Light in grainy profile pics, until: Bam! We “matched” with a trio of very attractive 30-something men. “Quick, let’s send them a message,” my friend slurred over our third pitcher as we watched football at a bar with some friends one cold Sunday night. Another less beer-saturated friend leaned over to peek at the guys’ pics. “Um, I think these are stock photos,” she said. We squinted at my phone. Was she right? Their photos were slick and well produced—one looked like a damn GQ spread. Getting catfished by an iPhone application would be a new low. We sent them a message anyway. We’re still waiting to hear back. Perhaps because our own photos weren’t exactly…fashion magazine-worthy.

Next came the Cambridge-based Singled Out. Like Who’s That, Singled Out pulls info from Facebook, automatically choosing your profile photo and, for some reason, listing my high school as my highest level of education, an error it wouldn’t let me change. It positioned my photo—in which I’m dressed as Sonic the Hedgehog for Halloween—so that all that was visible was one bright blue elbow. I wasn’t sure there were many guys out there, on this app or otherwise, looking to date a big blue elbow without a college degree and didn’t have high hopes for success.

The idea behind Singled Out is to create a safe dating space for women, allowing female users to control the conversation by posting yes-or-no questions to which male users respond. A man can’t message a woman; he can only answer a poll question (“Do you have sex on the first date?”) and hope that she likes his answer—and his looks—and starts a conversation.

“Anyone normal using this app?” I posted. And waited. A day later, I had only two responses. Both said “yes” (I was dubious), and both were under 21 years old. One’s profile photo was a blurry picture of a dog, presumably his. Unless it was him. The other’s profile said he was 19, but he looked about 12. I half-heartedly posted a few more questions—“Are aliens real?” “Is this real life?”—and pulled a handful of responses, none from anyone who looked old enough to shave. I wasn’t looking to do jail time and quickly deleted the app.

A friend had told me about another dating site, Jess, Meet Ken, founded by a BC business school grad. Launched this past February, it aims to put female users in control by inviting women to “recommend” the single guys in their life to other single women. The idea is interesting: A woman knows a great guy who, for whatever reason, just isn’t for her. He could be a platonic friend, a sweet ex, a hapless co-worker—if she thinks he’s got the goods, and other women might benefit from knowing it, she can make a profile for him on Jess, Meet Ken, named for the founder, Ken Deckinger, who met his wife through a similar recommendation.

I made a profile on the site, then still in its beta phase, citing my likes (“beer, music, horror movies, coats, jokes, iced coffee, people who can hang, good grammar, dudes with tattoos, the Oxford comma”) and my dislikes (“waking up in the morning, romantic comedies, mornings in general, bad jokes, people who can’t take a joke, dudes with bad tattoos, people who can’t hang, jam bands, mean-spiritedness”).

“People who can hang?” sighed a co-worker, who had reservations about how I was selling myself. Given that I’m a firm believer in honesty in marketing (my OkCupid bio says I’m good at “making mix CDs, procrastinating, correcting your grammar, getting stains on a white shirt and finishing all the wine”), I pressed save and assured her that this was indeed the person I wanted to present to the world. Surely this, the most promising of the sites and apps so far, would prove fruitful.

Think again. Most of the guys on the site were very young (noticing a trend here) and very not my type. (Think lots of sporty finance types. I tend to like ’em artsy and broke.) After scrolling through the posted men, one of whom was recommended by his mother, I settled on three. I sent friendly introductory messages to the women who’d recommended them—two friends and co-worker, respectively—and…waited. I’m still waiting.

At this point in my adventure I was disillusioned—both with online dating and with my own ability to even get a damn date. Was I completely and utterly hopeless? I was almost ready to give up. Then I heard about Three Day Rule, a self-professed modern matchmaking service headquartered in LA, with matchmakers in New York, San Francisco and Chicago, and newly launched here in Boston.

If joining OkCupid and Tinder had initially smacked of desperation and general ineptitude, joining a matchmaking service seemed downright insane. However, I was determined to find a decent date—if not for my love life, then for the sake of this story. So one rainy afternoon, I found myself sitting in the Mandarin Oriental’s ornate lobby across the table from my matchmaker, McKenzie, a friendly, pretty blonde about my own age who assured me she would find my inked-up Prince Charming. I was skeptical, but intrigued.

Named for Vince Vaughn and Jon Favreau’s characters’ dating rule in Swingers, Three Day Rule is a thorough, carefully curated service: You tell your matchmaker who and what you’re looking for—physically, emotionally, cosmically, whatever—and they go out and find it, meeting with the potential match in person before making a connection. It’s usually at least a six-month process, but McKenzie had just six weeks to find me my ideal man. Our deadline looming, we got to work.

First, we covered my past serious relationship history (none to speak of!), my dating history (a lot of drunken, casual hookups—sorry, Mom and Dad!) and, finally, what I was looking for at this juncture in my life (a guy who can…hang). McKenzie seemed more intrigued than horrified—I think she was up for a challenge. Next, she asked me to outline what I was into physically. Tall, but not too tall. In shape, but not beefy. Lean, but not skinny. Fit, but the type of guy who’s more likely to spend his weekends in a dark bar than out for a jog. Slightly alternative looking. Cool shoes. Ink. As I rattled off my increasingly ridiculous requirements, McKenzie took notes. “Must not love sports.” “Makes decent money, but preferably in a creative field.” “Doesn’t care about his looks, but, you know, looks awesome.” “Doesn’t wear a suit to work.”

It was becoming increasingly clear that the biggest problem in my dating life was me. As I quietly worried that I might be insane (and the genteel older couple seated next to our table likely wondered the same), McKenzie took measure of the monumental task she faced. Astoundingly, she seemed optimistic. At least one of us was.

She sent me on my way with the assurance that she’d have found, if not my dream man, then a cool enough guy within the next two weeks. She had even come up with a tagline for her search: “Indie rocker who can pay the bills.” Meanwhile, she offered to set me up with a dating coach and a stylist if I wanted a pre-date makeover, both perks of Three Day Rule’s service. I declined the makeover but took her up on the offer to speak with a coach—it seemed like I needed one.

I spoke with my dating coach, Kim, who’s based in LA, over the phone. We chatted for almost 45 minutes, during which time she tried to get a feel for how I usually approached dates and picking up guys in general. (Zero expectations and a lot of cocktails.) She had some suggestions.

“Think about the bar like a party you’re hosting,” for one. Meaning, be the vivacious center of the room—the hostess with the mostest that everyone wants to talk to. Then she gave me a homework assignment. That weekend, I was tasked with practicing the “five-second smile” on a guy I found attractive at a bar: Catch a guy’s eyes, hold them for five seconds, look away, then look back and smile in what I imagine is meant to be a come-hither way. Since I tend to be more comfortable standing with my back against the wall and my eyes cast down into my beer than eye-canoodling with dudes at my own private bar party, I was leery, but agreed to try it. It wasn’t so bad! (Though I’m pretty sure my “come-hither” could use a little work. OK, a lot of work.)

Finally, it was time for the Big Date. I was to meet [name redacted for the purposes of not being a total dick] for drinks and, hopefully, some decent conversation. I was terrified.

Meeting someone you know only through photos and messages on the Internet is weird enough. Meeting someone another woman picked up on your behalf, whom you have never spoken to, is some next-level strange. However, despite all my past dating fails, I was eager to see who my matchmaker had found. She’d “scouted” him outside a show at local rock club, showed him my photos, told him a bit about me (sugar-coating smoothly over some rough spots, I would assume) and essentially asked him if he’d be up for going on a date with some chick he’d never met. Incredibly, he was.

McKenzie prepped me for the date that afternoon. Be open-minded, she implored me. (I’d expressed some reservations that he didn’t fit my exact type, according to the photos she’d sent my way.) She described this guy as cool, sarcastically funny and, most important, a dude she truly believed could hang. I promised open-mindedness and headed out.

The person who showed up for the date was pretty much as advertised. Cuter than his photos, fairly sarcastic—definitely down to hang. One drink turned into seven, and I found myself genuinely having a pretty OK time.

The point of this whole—weird—thing, I think, is that sometimes there is no point. Sometimes you go on a date that you’re excited about and it’s a total bust. Sometimes you just score a few drinks and some sex. Sometimes you go on a date you’re not at all excited about and it ends up pretty OK. Sometimes you’re just sending messages into an Internet void. But it really is important to be open-minded—both about what you want and how you go about finding it. Maybe you meet a prince. More likely you end up making out with a horny toad. It’s important to remember, though, that there are just as many weirdoes online as there are in real life. I find that strangely comforting.

As for the date, we’ve made plans to hang out again, and whether there ends up being that kind of chemistry, I’m at least confident there will be beers and some laughs. We’ve been texting. I’ve yet to receive a photo of a marine mammal of any kind.