The Hook Up: Can you “fail” at online dating?


So after several failures dating IRL (I wrote to you last year when I was heartbroken) I have followed my many queer friends’ advice and delved into the world of OKCupid.

The problem is, I think the premise is that people date multiple people at the same time. I can’t focus on more than one person at a time! I don’t know what to do. And if someone is really cool, I tend to latch on to them because I am so used to not seeing or knowing anybody I want to date. I can’t get my head out of the monogamous pothole, and I tend to get a little uncomfortable if I know the other lady is dating other people at the same time. I try to be cool with polyamory but I’m not! I don’t like the idea of dating a whole bunch of people at once. I tend to put all my eggs in the same basket.

Do I fail at online dating? What do I even do? I lied about my thoughts on polyamory on my profile just because I have no effing clue what’s normal on an online dating site and what’s not. — No-kCupid

Anna says: Fear not, No-kCupid, you can’t “fail” at online dating anymore than you can fail at going to the grocery store. Everyone dates differently, and everyone uses dating sites differently as well. Some people are looking for their #1 Soulmate Forever, some are looking for something to do this weekend, and some are, as I found out the hard way, simply looking for people to go rock climbing with (that was not the kind of “activity partner” I was interested in pursuing). The good news is that you can use OkCupid any damn way you please. No one is going to boot you from the site because you’re looking for a monogamous partner. Similarly, you should never engage in something that makes you actively uncomfortable just because you think you should be comfortable with it.

It can feel like polyamory is the hottest thing since Pound Puppies, especially on OkCupid, since more and more people are openly talking about it, but that doesn’t mean you have to jam your square peg into a bunch of peoples’ round holes if you don’t want to. One of the major perks of online dating is that you can be really specific about what you’re looking for. You have a platform where you can say anything you want. And actually, the more direct you are, the more likely it is you’ll meet someone who’s an excellent match. Within reason. If you get too specific then you’ll start alienating potentially awesome people. Avoid segregating or stereotyping people, such as: “I’m looking for a blue-eyed Hungarian vegan who’s 5’2’’ or less and promises to never take me to a Pixies reunion concert.”

That said, it is common to assume that people on dating sites are going on dates with not just you. You can’t altogether avoid the possibility of your dates dating other people, but you can try to narrow it down by choosing to go on dates people who are more monogamously inclined or looking to date that way. It won’t make you an OkCupid leper, I promise. It only makes you honest. Approach dating the way you would approach anything important in life. Doing it any other way than the way that resonates with you will only serve to make you sorry later. You can even phrase it in a romantic light, if the term “monogamy” is too much of a profile boner killer. Because it IS romantic. Wanting to spend all your time with one person, and the “I only have thighs for you” sentiment are very common staples of how we view romantic relationships, even if they’re not that realistic.

If monogamy is your truth, then own it. To hell with what’s “normal.” Normal is a city in Illinois that no one visits. So no more lying, OK? If you’re gonna do this dating thing, you gotta do it full-throttle, no excuses, no bullshitting. You gotta do it with humility and nerve and audacity and an open mind. Nothing else will do. This is your life after all, and your heart. Don’t put it on the line for anything less.

Dear Anna, I’ve been in a relationship for three months now and things are starting to get quite hot and heavy, but I haven’t admitted to my partner yet that I’m a vagina-virgin. We talked earlier on about our relationship history, and I told her I had been with another girl for six months, so she might’ve assumed we had at least had sex. Truth be told, the ex and I got to heavy (HEAVY and half-naked) grinding, but I wasn’t comfortable enough to go the extra mile. But I think my girlfriend’s been assuming I had crazy sex and know my way around the lady landscapes.

Now, I feel like my facade is that of an “experienced” dyke, even though I don’t know the bare minimums of lesbian sex. I don’t even know how to navigate the waters of who should do who first (is it rude if I get impassioned and distracted and self-centered right away, forcing her to wait until after I climax?). I’ve seen enough episodes of The L Word to know that sex can be extremely sensual and harmonic (e.g. Bette and Tina), but I have the sense of reality to know that it doesn’t always work out that way (e.g. Dana and Jenny), especially if it’s your first time.

My girlfriend and I won’t be able to keep our clothes on for that much longer (she’s fucking HOT like tabasco) so it’s only a matter of time before we’ll do the dirty. How can I pull it off without being caught and denigrated as a “baby dyke”? I’m afraid little sexual cues might give me away, like being too selfish right off the bat or not giving oral the way it’s normally given (disclaimer: I’ve never gone down on a woman, I have no idea if there is a “standard” or “guide,” but in every lesbian film/show I have seen, regardless of who performs it, it always seems to illicit the same response — an orgasm). How should I play this? — Coyish Cunner

Anna says: I chose your letter and the one before it for a reason. You both seem very preoccupied by the notion of normalcy, which I will tell you straight away doesn’t exist. This is good news! It means there’s no right way to go down on a girl, no right way to have sex, and there’s no right “move” that every lady enjoys. The bad news, however, means that because there’s no Gold Standard of how to please a lady, you have to figure it out anew with each new person, by talking about what you both like to do and trying things out.

I would suggest you start talking, Coyish Cunner. Talk while you’re getting heavy, talk after it’s over, talk about sex in nonsexual settings (I recommend IHOP). The more comfortable you are talking about your desires and fears and anxieties, the less they will weigh you down during the act of sex itself. And drop the facade that there is an Utmost Authority on All Dyke Sex Ever. There isn’t. There’s just all of us, naked, in the dark, fumbling at zippers and hoping that things turn out okay. (That’s me in life generally, too). Being inexperienced is not a handicap. Assuming that you know everything your partner likes without asking them is. Your girl might not even like oral sex (some lesbians don’t).

Reducing those first time jitters will be much easier if you have a vague notion of what your partner likes to do. While we’re on the subject, let me also take this time to suggest that you never, ever compare real sex to what happens on The L Word. ‘Cause that sex is fake, darlin’. Those oohs and ahhs and orgasms are all scripted. Real sex is messy and awkward and it’s extremely rare for both people to come at the same time.

Good sex doesn’t happen by accident. People don’t fall wordlessly into a sea of effortless orgasms. It takes time and practice and LOTS of communication. So worry less about who should do whom first. There’s no script to follow. Trust your gut, trust what feels good, and check in with your partner if it seems like things aren’t jelling. You’ll be great, I’m sure. If your hot and heavy not-quite-sex sessions are as hot as you describe, then the rest will be too.

Readers, any other advice or encouraging words for getting over first time nervousness?

Hailing from the rough-and-tumble deserts of southern Arizona, where one doesn’t have to bother with such trivialities as “coats” or “daylight savings time,” Anna Pulley is a freelance writer living in San Francisco. Find her at and on Twitter @annapulley. Send her your Hook Up questions at [email protected].

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