Frisky Q&A: Dating Blogger Maura Kelly Dishes On Her Year Of Living Flirtatiously

Maura Kelly has a unique job — she blogs about her dating life for Marie Claire. Her column, “A Year of Living Flirtatiously,” is a frank, humorous, self-deprecating account of her travails on the front lines of dating. The project started when Kelly realized that if she approached finding a man with as much zeal as she approached finding a job, she might find the man of her dreams. So far, no such luck, but here she shares with The Frisky her best dating advice, the weirdest date she’s been on thus far, and why what men really want is to be treated like a woman. The Frisky: How did “A Year of Living Flirtatiously” come about?

Maura Kelly: A few months before I got the blog job, I was out at Bar Tabac in Brooklyn’s Cobble Hill, where some sexy stranger seemed to keep looking at me. I was feeling increasingly excited and terrified when some other random portly guy came over to me and my friend. We tried to be polite as he showed us cell phone pictures of his dog — and totally blocked my view of you-know-who. While I was gritting my teeth and nodding about how, yes, Fido was outstandingly cute, the sexy guy came over and handed me a Heinekein. “I just ordered this but I’m not going to drink it,” he said. “So I’d like you to have it.” And then he walked out the door. I considered running after him, but I wimped out — and then totally regretted not taking a chance.

Back then I was nervous about flirting even to the extent of naturally maintaining eye contact. I’ll think, “Well, I don’t want him to catch me looking at him, because then he’ll think I’m desperate or something!” I was terrified of taking any kind of risk. And yet, frequently, I was going out to bars and parties primarily in the hopes I’d meet a guy. But I was being totally passive about it. The amount of time I was completely wasting started to aggravate me. I started to think, “If this was my job, this dating thing, I’d never be so passive.”

So, the next thought was: “I should make this my job.”

The Frisky: Were you hesitant about putting your personal life out there for everyone to read?

MK: Yes and no. I got the job in part because I’d written a number of pretty revealing personal essays (including one about how, at age 30, I’d finally started masturbating). Doing that helps you develop a thicker skin, as well as a much stronger forearm. Also, I felt really excited about the idea of doing the blog, of trying to help myself (and other people) feel more control over their dating lives.

I wasn’t going to turn down the opportunity or make the blog suck by not talking about the gory details just for the sake of pleasing some shadowy potential-boyfriend-I’d-not-yet-met. Of course, those kinds of things are easier to say in the abstract. Since the blog’s started, it’s been tough when I meet someone I like and realize he’s going to read about a certain terrible relationship or a certain really embarrassing courtship.

There was also one saga — when the blog first started and I thought no one was reading it — where I spent a whole week agonizing over a guy in real-time, analyzing every little last bit of communication I got from him. And then we met up that weekend, and he was like, “Uh, yeah, I read the blog.” That was the last time we hung out.

The Frisky: What’s the most important thing you’ve learned about dating?

MK: There’s a lot of generalizations to be made about the dating game. At the same time, every person is so different that it’s best not to guide yourself with some set of hard-and-fast rules about what it “means” if he does such-and-such or how long you should hold out to have sex. Each situation is sui generis, so try your best to go with your instinct and navigate it on its own terms.

The Frisky: What are the biggest mistakes you think women make, dating-wise?

MK: I don’t want to phrase it that way. It implies there are glaring errors women are making, and if only they corrected their ways, their lives would be perfect. Dating is not easy, which is why there are so many articles, books, blogs, and how-to videos about it. As a perennially single person, I hate it when some person thinks he or she has the magic piece of advice that will cure all my woes. It’s just not that easy to snap your fingers and — poof!– suddenly find the perfect relationship.

For both men and women, dating is pretty hard, maybe harder now than ever, because there is no agreed-upon set of “rules” we can refer to, to help us interpret what a certain behavior means. Between open relationships, late-night texting, and discovering that your crush might be dating six other people via his Facebook status updates, I think it’s really hard for anyone who’s out there in the dating world to really know where he or she stands — at least until they reach an exclusivity agreement with someone, at which point they’re no longer “dating,” since they’re in a committed relationship.

All that said, I will say that I think a lot of women give guys too much leeway. If he’s not responding to you, cut him loose. Don’t try to win a guy over if the situation has become fraught with anxiety for you. As a friend of mine likes to say: “Don’t play hard to get. Be hard to get.” Which is to say: Don’t operate according to some manipulative set of rules or tricks, but do have high personal standards. And if some dude isn’t living up to them, say sayonara.

I think so many of us are busy protecting ourselves that it’s really hard to get a read on anyone. I think we’d all be better off if we tried to be more honest with ourselves — and with the people we’re dating — about how we’re feeling. Of course, all of that is a lot easier said than done.

The Frisky: What’s your personal policy on sex and dating?

MK: You should do what feels right. It’s hard to make across-the-board recommendations. Don’t do something that makes you uncomfortable. And communicate with the person you’re dating. Tell him things like, “Look, I really like you and want to get to know you better, but I don’t feel comfortable going back to your place after only one date.” Or, “Hey, I’d love to have another drink at your apartment, but I don’t want to have sex tonight. I’d like to wait.” Or maybe it’s something like, “Sex!?!? Well, sure, let’s have some. Because I like sex, and you’re not so bad yourself. But before we do it, I’m just going to let you know I’d like to get a text from you tomorrow, just saying hello or something.”

The Frisky: What about online dating?

MK: It baffles me that anyone still attaches any kind of stigma to it. I cannot understand how anyone who’s been single for more than, say, nine days hasn’t tried it. Particularly for someone who works from home, like me, it’s a great way to increase your exposure to other single people. And I’ve met so many interesting, nice people I wouldn’t have met otherwise, many of whom I’ve dated for a few months and many of whom have become friends.

But my advice is to keep the electronic communication to a minimum before meeting up in person. No more than 10 emails (five sent and five received) and one fairly brief phone call, not longer than 45 minutes, to make sure he sounds sane. Don’t waste your time until you know what he’s like in the flesh — because he could be 100 pounds heavier than his pictures, or six inches more bald, or have a bizarre fetish. Or you could simply lack chemistry. Plus, it’s easy to let our imagination override the facts.

The Frisky: What is the weirdest date you’ve gone on so far?

MK: Honestly, I’d like to go on a few more weird dates. So many dates are just the usual boring recitation of resumes, favorite colors and observations that I feel like I’ve made a thousand times. I’d love to say to a guy, “Hey, let’s take a week before we meet to read the same book so we can discuss that on our first date.”

But there was this one guy — we went into a restaurant and the first thing he ordered was a banana.

Oh, and another guy, from the former USSR? Let me preface this by saying I’m one of the least intimidating people anyone will ever meet, although I was a little more put-together for my first — and only — date with this character than I usually am, because I’d just been at a Marie Claire photo shoot. So when I showed up, my hair and makeup were professionally done.

Anyway, over dinner, this guy tells me how he’d basically been stalking someone. Then he said something along the lines of “Don’t worry — you’re not pretty enough for me to stalk you.” Not literally, but close. I’d broken up with someone I’d really cared about only a week earlier, but I was determined not to get right back out there into the dating world, so I was a little emotionally unstable to begin with. I went into the bathroom and bawled for a good 15 minutes, uncontrollably, until I knew it had gotten weird. When I finally returned to the table, my face was swollen and splotchy. He knew. He took my hand from across the table, asking if I was OK. I started crying again. And he said, “See? I like you so much more now that I know you’re human.” I heard from him again after that, but when I didn’t respond, he didn’t stalk me, and maybe I was ever so slightly disappointed.

The Frisky: What’s the best way to let a guy know you don’t want a second date?

MK: In a secular way, I’m pretty committed to the golden rule: Treat other people the way you’d like to be treated. At no time is this easier to do (and more essential) than when you’re in the position of power. Think about how you would feel if you’d asked someone on a second date and he didn’t want to go. Wouldn’t you like to be let down easily, promptly, and kindly? Well, so would any guy, if he’s got no chance with you. I really don’t understand why so many women complain about how guys can be such jerks, and yet so many of us seem to think it’s fine for us to be jerks to dudes when we’re not into it! I think part of the reason is that it can be annoying to be asked for something — your time or affection — that you don’t want to give.

Put yourself in the guy’s shoes for a second. Then write a nice email, highlighting all his good qualities, but explaining that you just didn’t feel the ol’ ineffable spark. Be honest and firm. Don’t say you’ve got a busy month or that you’re having a hard time getting over your ex. If you think there is no possibility you’ll change your mind about him, trying to make him believe the problem is bad timing isn’t doing him a favor He’ll think he might still have a chance eventually.

The Frisky: What are your dating resolutions for this year?

MK: I’ve personally resolved to ask for what I want a little more often, before I hem and haw and hesitate for so long that whatever it is — like seeing someone more than once a week — becomes a really big deal.

I can fall into the mindset that a guy should be making all the plans or the suggestions, and if he isn’t, I tend to get really anxious and crazy, and then I cry, and then he’s like, “You’re crazy — I can’t do this.”

It’s hard for me to believe I “deserve” love, but I’m trying to work on reminding myself that, deserving-ness aside, a relationship in which I feel unhappy far more often than I feel happy is a waste of my time.