7 Days of Creepy and Exciting Online Dating ...

A few months ago, I realized something troubling: I haven’t been on a real date in ages. By “real date” I mean that a guy I know hasn’t called me, asked me out a few days ahead of time, picked me up, done something together, then dropped me off, in (literally) years. Sure, I’ve “hung out” with guys. I’ve even had short-term boyfriends. But a date? I was beginning to think they were extinct, like answering machines and VHS tapes.

Feeling emboldened by a nasty break-up, I decided to completely revamp my dating life. But where to start? The first obvious step in dating is meeting men, but where does a nearly-40 girl meet eligible men? Turns out, there are really three places: online, on blind dates, and “organically” (making connections with men I see as I go about my day). I’m not the bravest girl, and am actually somewhat shy, but I thought, why not? Why not go for a dating experiment, spending one week focused on each of these ways to meet men, with a week off in between… thus, Jen’s Dating Experiment was born, perhaps the best and worst idea I’ve ever had.

Week one is online dating. I jumped in, feet first, and here’s what happened.
Day 1: Creating my online profiles
I gathered my most flattering photos, and jumped online to spend four hours creating 7 online dating profiles. Why can’t I copy and paste my profile information from one profile on one site to the others, too? I registered with Fellody, eHarmony, Match.com, Perfect Match, OK Cupid, Plenty of Fish and Zoosk. That’s a lot of dating sites, I know, but if you’re going to do it, do it all the way, right?

Before I even finished posting my profile on Plenty of Fish, I had three messages in my inbox. Within half an hour of posting on eHarmony and Match.com, I had several messages there too. Sadly, eHarmony and Match.com charge a pretty stiff monthly subscription fee (about $40 each) to see your messages or to respond to them, or to contact anyone you happen to be interested in. I felt bad for not being able to respond to the poor guys who were interested on Match.com and eHarmony, so I deleted my profiles.

Truthfully, I wanted to delete my profile from Plenty of Fish, but I vowed to give it a chance. Why, you ask, was I so ready to delete my profile after only one hour? Because every single one of the messages I got that first day were creepy. And weird. And creepy. But, I figured, that’s what the delete and block options were for, right?

Setting up my Fellody account was easy, and I absolutely love the idea of the site — you’re matched to guys based partially on your musical tastes. You upload your iTunes library list. Then Fellody does the rest. The site is vibrant and colorful, and I wish I could say more, but I never found anyone close enough to me to make a match. (I have to admit I love the idea of having Groupies, though I'm not sure yet what those are.) My nearest match lives in Cleveland, Ohio. But I really like the site, so I’m leaving my profile in the hopes that someday soon, it will gain popularity outside of Europe, which is where most of the users are right now.

Next, I tried Perfect Match. Again, it’s very easy to register, but there don’t seem to be many users, at least not near me. I decide to leave my profile up anyway. Same with OK Cupid.

Then, there’s Zoosk. It was impossible to complete my profile. When the site sent my confirmation/verification email, I clicked on the link and got the strangest error message, something about not having any ice cream. Whatever. I did a little research and found that Zoosk also requires you to pay a subscription fee to contact other users, so I didn’t even attempt to complete my profile there.

At the end of today, I have four online dating profiles. Let the fun begin!
Day 2: Meet the Creepsters!
Okay, I can’t handle any more of the creepsters on Plenty of Fish. I’ve gotten, literally, about a hundred messages from guys who think it’s appropriate to start a conversation with me by saying “hey sexy,” or worse. I decide to take a break from my inbox and start doing a little searching on my own. I comb through my potential matches and, after an hour, I have three potentials. I add them to my “favorites,” not realizing they’re informed of this. One of these cuties contacts me. We message back and forth, and he asks me to meet for coffee… in an hour. Should I go for it, or, against my spontaneous nature, play a little hard to get? I decide to meet him and he IS cute. And nice. And articulate. After our coffee date, I give him my card. Then I get home, log back in to Plenty of Fish, see several more messages (one asking me for nude photos), and impulsively delete my account here. I can’t take it anymore. It’s a sewer here.

Still nothing from Perfect Match or Fellody.

One message from someone on OK Cupid. I look at the site a little more closely, since this may be my last active site for the rest of the week. It’s not bad. I like their matching system. Hmm.
Day 3: Getting Used to It
Dinner date with the ONE guy from Plenty of Fish. I like him more than he likes me, which is a very good sign, actually.

A few little hits on OK Cupid. Nothing too impressive. I’m still day-dreaming about the guy, the one from Plenty of Fish. Enough, Jen!
Day 4: Weeding Through the Weirdos
Still day-dreaming about Plenty of Fish guy. But I have work to do, and since he’s not too attentive, I’m assuming he’s not as into me as I am into him. That’s okay. I still like flirting with him via text message, and who knows where it could go? I run a background check on him, and stalk him on Facebook, just to make sure he’s not holding back because he’s got something to hide. Nope, he doesn't.

In the meantime, I spend more time combing through the matches OK Cupid has set aside for me. I can sort them however I want, and after an hour, I have three potentials, though I know straight up I’m not hip enough for one of them (but I send him a message anyway because I’m feeling bold). The other two I do message. They’re nice. I set up an ice-cream date with one. The other doesn’t really respond with any depth.
Day 5: Status Report!
The guy from OK Cupid who I was certain I wasn’t hip enough for? He messaged me and we exchanged witty and clever messages back and forth for a couple of hours. It feels good to be on, and charming. I know he’ll never ask me out, but this is fun! It makes me feel bold. Suddenly online dating isn’t creepy. It’s interesting! It’s exciting! I like it!

Finally, a message from Fellody, but he’s in India. Sorry, no match. But we do have similar taste in music, which is cool. I really hope Fellodytakes off here in the States. It’s such a good idea!

Still nothing from Perfect Match. Am I unmatchable?

The guy from Plenty of Fish and I are still exchanging sweet though infrequent texts. Yes, I am really much more into him than he is into me. *sigh* Apparently he's offended that I ran a background check on him before I agreed to meet him. He was squeaky clean, and it wasn't a credit check, so I don't know why he was so put off. Maybe I shouldn't have TOLD him I ran the background check?
Day 6: An Ice Cream Date
Nothing from the hipster on OK Cupid, but I’m still feeling brave and buoyant. I knew he wasn’t interested in a meeting in person, so I’m okay with it. I do wish this site had more men on it. It’s free and I like the way the site works. And I do still have my ice cream date later this week with one of the guys from here.
Day 7: Should I Stay?
This is my last day of the week on online dating, and I have to decide if I’m going to keep any of my profiles, and if so, which ones?

I’m going to delete Perfect Match. There just aren’t any guys on there, and it’s a lot like the other sites out there.

I’m going to keep OK Cupid, at least until after my ice cream date. And since this afternoon, I’ve been chatting online with a guy who seems (keyword being “seems”) to be nice and normal and intelligent, I’m feeling a little hopefully about this site.

I’m also going to keep Fellody, because I fervently hope it takes off here in the States. I really like the idea of match-making based on music.

That’s my week of online dating. If I had to choose three words to describe the experience, I’d say creepy, interesting, and emboldening. There are loads of creepsters out there, all of whom seem to have a laser focus on one thing: sex. If possible, anonymous kinky sex with as many women as possible. I did connect with a handful of men in my week that were interesting, intelligent, and nice, so they’re not all pervs — you just have to be prepared, and picky. And patient. And there is something very liberating about online dating. First of all, when you’re creating your online profile, you’re forced to think about what you want in a relationship, something we all ought to be doing, but few of us actually DO. Second of all, the flirty banter and good conversation help build your confidence, and hone your skills, long before a date-type situation, which is helpful. And last, it’s never boring. Where besides online dating can you make a sweet, innocent ice cream date with a truly nice guy, and ten minutes later, be propositioned by a perv asking for nude pics? My advice: give it a try. Just be careful.

Now, a week off, then on to week 2 of Jen’s Dating Boot Camp — 7 blind dates in 7 days. Stay tuned!