Online dater | Hillary’s diary

The 27-year-old law student records her online dating experience with eHarmony.
Photograph: Christopher Kitahara
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Online dating Hillary, 27, Lincoln Park, straight

After nine months of playing the dating-site field, Hillary realized she “was only attracting mustachioed guys who oozed Kerouac” on OkCupid and the breadth of Match’s subscribers was just too overwhelming. She’s now focused on finding love (or at least a decent dinner) on eHarmony.

December 11 There were several interesting guys in today’s “crop” (eHarmony only provides you with a handful of matches each day). One listed “talking to my family on the phone” as an interest. Another wanted people to know he had all kinds of dog-clad boxers, including a pair featuring dachshunds in sweaters. I can be guilty of a filterless persona, but in the world of online dating, it can be difficult to let your personality shine through without scaring people off. Your underwear-preference disclosure might be better left to date No. 5…or No. 15. I’ve exchanged e-mails with a couple of guys who seem nice, but no dates set yet.

December 12 While walking home, I made eye contact with a guy I went on one date with. This is not nearly as awkward as the time I had to play volleyball against a guy I had had dinner with a few weeks prior. (For the record, my team won.) Chicago, for as diverse and wonderful as it is, tends to be very segregated. I consider dating someone living in Wicker Park a long-distance relationship. I’m punished for this viewpoint by running into people I’ve dated on a fairly regular basis.

I responded to several of the more promising guys in the day’s batch. The number of men who match what I’m looking for diminishes the longer I’m on eHarmony. I’m looking forward to the postholiday blues, when men everywhere, beaten into submission by nosy relatives, and vulnerable to eH’s commercials and promotions, sign up in droves.

December 13 I’ve been bad about responding to some of the e-mails. I find that I go in waves of interest and disinterest. I’ve also found that eHarmony’s process makes it really easy for me to sift through prospects. The site’s Guided Communication, which allows you to ask questions before facing the pressure of a full-blown e-mail, acts as a funnel: If I’m not interested enough to answer a question, I know I’m not interested in the guy. Some people I know would rather meet quickly than spend a week or two trading e-mails. But guys who suggest a phone conversation or date after one e-mail are generally too aggressive for me.

December 15 A few e-mails came in late last night. I’ve always wondered about people who e-mail at 1am. At work? Night owl? Late-night cruiser? One guy seemed nice enough, but kept referencing various pictures I have posted, including one I took down. It’s not that he seems skeevy, but it definitely makes me a little uncomfortable. I sent a few responses tonight that were a bit cheekier than I normally send. I’m worried they might have been a bit over the top, but we’ll see.

December 16 I took a break from online dating to attend Merry Mustachemas at a local bar. I wore a white mustache worthy of Col. Sanders. I also decided that the first guy to hit on me while I wore my mustache would win my heart. Alas, it didn’t happen. Heart still for sale.

December 17 Some guys are getting deeper with their initial questions. Talk of wanting children, asking if I’m proactive in relationships (is this a fancy way of asking me if I wait by the phone?)…these are important, deal-breaking topics (I think; I’m still unclear on the proactive question), ones that shouldn’t be broached via e-mail with a stranger.

I have a lunch date tomorrow with a guy I’m on the fence about. He’s seemed reluctant to pick a normal time for a date. I’m a lot more likely to give you a good-night kiss at night. A lunch date feels more like an errand.

December 18 The lunch date was pleasant. He drove the half-mile between his place and the restaurant, which I found odd. He’s a bit more of a gym rat than I typically go for. We shared an interest in vulgar rap and Big 10 football, but the chemistry wasn’t there. In the words of Jay-Z, “on to the next one.”

December 19 Guys who have a serious interest in martial arts have been e-mailing me in disproportionate numbers.

December 20 One guy has suggested we meet at a nearby Lebanese spot for dinner and conversation. He gains points, not only for knowing a Lebanese spot, but being willing to eat there. I love cooking and food, and any guy who loves those things can’t be too awful, right? Unfortunately, this date has to be put on hold for the holidays.

December 22 When you display your life for the dating world to see, you’re bound to discover common quirks and habits that give the illusion of a deeper connection. I’ve bonded with guys over a shared love of Vonnegut, similar birthdays, Northwestern football. Simultaneously murmuring “Topo Gigio” à la Tim Allen in The Santa Clause as you pass the same-named restaurant in Old Town does not a life partner make. In fact, that one lasted about a month. At the end of the day, shared hobbies and interests aren’t as important as mutual respect, shared values and (in this town) NFL allegiance.

December 25 Santa brought me six new matches! As I didn’t bring my laptop home for the holidays, and flirting on the eHarmony smartphone app is rather tedious, I shall have to wait until I’m back in the safety of my apartment to unwrap God’s gifts to women.

December 27 From my phone in a gas station parking lot, I edited down the 30-plus new matches that had accumulated in my absenceEasy edits for me are generally location (I have no car, so the suburbs might as well be Alaska), and attraction. I’m only human. A carless human.

December 28 Sometimes online dating feels like a part-time job. While you might spend hours standing around in bars looking for Mr. or Ms. Right, at least in a bar you can drink and dance and spend time with friends. Online dating from your couch on a Sunday night can be downright depressing. Then again, cruising for guys in a bar on a Sunday night might be just as depressing. Pulling the trigger that takes you from e-mail banter to real-world interactions is also pretty nerve-wracking. That’s where I am with Lebanese-restaurant guy. I’ve also received a few “invitations” to “call or text if that’s easier [than continuing to e-mail].” This aggravates me. If you want to talk to me on the phone, ask for my number and ask to call me. Don’t put the onus on me under the guise of my “comfort.” It’s too late to send any e-mail responses tonight. One guy’s questions (e.g., If you could accomplish only one thing during the rest of your life, what would it be?) are too exhausting to even contemplate.

December 29 Today’s batch of men included the roommate of a guy I exchanged a few e-mails with back in September, and a guy whose pictures included a girlfriend of mine. I didn’t know how to process this other than to close my computer and have a glass of wine.

January 1 Much like the people infiltrating your gym, the New Year brings online-dating resolutionists. In a quick survey of commercials, I guess it was either this or Weight Watchers.

January 2 I caught myself differentiating between dating online and “in real life.” They’re really just different ways to spell awkward. A few months ago, a girlfriend and I decided during predinner drinks that we had forgotten what it was like to meet men in bars. Perhaps emboldened by said drinks, we struck up a conversation with two seemingly nice men leaving the sushi spot where we were dining. They ended up eating a second “dinner” to stay close, and telling the waitress to put our dinner on their tab. This unexpectedly sweet gesture might have gone a long way had one guy not tried to later “collect” on it with wandering hands. We decided that meeting men was a laborious, sometimes awful process, no matter the medium.

January 3 The good thing about eHarmony’s Guided Communication is it helps to weed people out almost as effectively as their profile information. A while back, a guy asked me which character from Lost I would most like to have dinner with. I’m sure he’s a very nice guy—a very nice guy who finds connection and value in a show I’ve seen 12 minutes of. Tonight, a guy asked me how much value I place on premarital sex. Next.

January 4 For dinner tonight, I met a guy who I’d been exchanging e-mails with for a few weeks. We seemed to have a fair amount in common: We’re both runners who have close relationships with our siblings. While dinner was pleasant, he asked about my experience online dating. I’ve always found that a strange (and frequent) conversation to have on a first date. I once had a guy high-five me for looking like my picture. Online dating can be the elephant in the room on a first date, but addressing it is still an inquiry into my dating life. I can’t help but feel like a second-class dating citizen, subject to different rules of manners and social awareness. You may have met me online, but please show me the same respect you showed the girl you met at a dinner party and refrain from asking how many dates I’ve been on that week. My date tonight was a perfect gentleman, and his inquiry into my online dating experience seemed to be a way of nervously moving conversation forward. There will be no second date because we weren’t compatible, not because he broke the fourth wall.

January 5 After a few weeks of less than promising options, I’ve decided not to continue my eHarmony subscription when it expires in a few weeks. The past nine months have taught me that I’m just as likely to land a date at a bar or via Twitter as I am on the site. At least I haven’t resorted to Craigslist.

January 6 For whatever reason, this Friday night was filled with men. Nights like this, usually accompanied by a full moon or a Pacquiao fight, always make me a little weary. A few minutes into my night, a bearded man tapped me on the shoulder and drunkenly stumbled through an introduction. He persistently tried to buy me drinks, dance and “re-introduce himself” over the next 45 minutes. I went from flattered to frustrated.

January 8 I was just matched with my ex-boyfriend’s roommate. Out of wine, I resorted to banging my head against the wall.

January 10 A friend sent me a link to a study that found that Europeans on dating sites are less likely to click on a Kevin or Chantal than they are a Jacob or Charlotte. No word on where Hillary falls in the date-o-meter. In other news, I’m officially the friend people send online-dating articles to.

January 11 Online dating gets an undeserved bad reputation. Guys I’ve met online even have been distrusting of the process. Because of the steady influx of matches, it can be exhausting. Answering questions about yourself and making small talk are inherent in dating; however, in the context of online dating, this process is magnified and accelerated. I know three couples who met their spouses online. While it may not have worked for me this time, it does work. The biggest lesson I’ve learned is to throw out the rules and be open to love, regardless of its origin…as long as it’s not Craigslist.

Want to date Hillary? E-mail hillaryd@tocpersonals.com.

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