You keep writing and asking for my advice on how to Internet date successfully. I don’t know what more I have to do to convince you that I am not the person for this task. Last week, a girl I’ve seen several times apologized for not being able to call me back in the last three days because she left her phone at home that morning. That doesn’t make any sense whatsoever. And you’re trying to mimic the steps that I’ve taken to get me where I am today? I feel sorry for you, I really do. It’s like asking Larry King how to run a lively talk show that’s appealing to viewers of a variety of ages and racial backgrounds. Misguided at best. But as I’ve said before, hey, I got the time. So here we go…
Q. “I work a lot so I don’t many nights free for dating. Recently I’ve started setting up a bunch of dates on the same night at the same bar. One girl at 7, another at 9, another at 1030. But what do I do if one runs late and the two girls bump into each other?” F. Clark; Sacramento, CA
A. Uh…kill yourself? I think kill yourself is my answer for this one. Either that or write down everything that happens and turn it into a hilarious romantic comedy starring a Wilson brother and Drew Barrymore. Because that’s the best case scenario.
I will admit that I’ve had multiple dates on the same night, but at the same bar, dude? Is it really worth it? Is it so valuable to not have to take 15 minutes to go to a different bar that you’re willing to accept the risk of two girls finding out that you’re assigning them slots like an air traffic controller and then teaming up to cut off your face? I’ll end the suspense – no, F. Clark. It is not worth it. Keep it to two dates per night MAXIMUM, and plan them in separate locations, jackass.
Q. “I’ve had my profile up for a few weeks and nobody is writing me! What’s the dealio?” J. Klern; Houston, TX
A. Perhaps it’s your stubborn insistence on using the word “dealio.”
Look, the vast majority of questions I get about Internet dating revolve around this general complaint: “I am charming, I am beautiful, I am brilliant. Why doesn’t anyone ever write me.” If you’re a guy, then you have your answer. Girls don’t write guys, unless they’re capital C Crazy. If you’re a girl, then it’s because your profile stinks. Sorry to be blunt, but it’s how Larry King would handle it.
Sorry, Minka Kelly. Not until you work on your profile.
I often come across women that I’d like to write because, well, they’re attractive, then I sit there staring at their profile for 10 minutes desperately trying to come up with something to say. Sometimes I just go with “So, you’re into having fun and laughing? Me too! Let’s have intercourse.”, but usually I just give up and look for someone else. If you can’t think of one interesting thing to say when you’re under no pressure sitting in your living room wearing your jammies, then something tells me you’re not going to be so great on a blind first date. And just throwing a bunch of words at the problem and hoping something sticks isn’t the answer either. Here’s a profile I read last night…
“I love to laugh and have fun. I’m happy and I’m always looking for a new adventure, I have a ton of energy and I like to be active. I like to go out just as much as I like to stay home. I love to travel and explore other countries and I would want someone I’m with to also enjoy that. I’m looking for someone who is laid back but driven and also likes to get out there and do things.”
Plenty of information there, lots of different topics and areas of interest – and all of it unfathomably uninteresting. Try writing that person an email and tell me what you come up with. “Hey, your profile really caught my eye as I am laid back but at the same time driven and…I like people with…energy? Let’s have intercourse.”
Honestly, J. Klern, if people aren’t writing you, it’s probably because your profile isn’t making it easy for them. Read yours again and see if you’d email you. If not, talk about your most eccentric dislike or crazy preference, whatever you think is most likely to start a conversation and go with that.
Or you could just post some nude pics. That never hurts.
Q. “I think we should go out.” S. Geil; Weston, Washington
A. Ok, but fair warning, I’m bringing Larry with me.
Q. “I’ve been talking to this guy who seems really cool but he only has one picture up online, and it’s kinda fuzzy. I asked him if there was anywhere I could see more of him, and he sort of dodged the question. I don’t want to be shallow, but I want to make sure we have a physical connection. What should I do?” T. Lane; Maine.
A. It’s not shallow to want to be attracted to the person you’d be going out with. Don’t apologize! Why do people always apologize for wanting to find their mate attractive? Wait, that is a question and I am clearly writing in the “A” section of this post. Apologies for the confusion.
I once went out with a girl who’s picture looked more or less like this:
And you know what – she was very cool and almost uncomfortably hot. So I would say that there’s a one in one hundred chance that this guy is very handsome, but that one in one hundred times has already been taken by me, which means you’re dealing with one of the other ninety-nine bozos.
There’s really no excuse for having only one picture nowadays, unless the guy you’re talking to is like 65 years-old. Or a vampire. And even then, he could get a buddy to draw a couple sketches of him or something. The guy you’re emailing is hiding his face – or the rest of him – for a reason, so I suggest you move on. Dot org. Got it?
Crap. That was another question. Sorry!
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It's Not a Match.com 
Wait, when did outgoing and self-confident turn into capital C Crazy? Especially if you’re emailing someone who claims to be looking for those very qualities? Has this been my problem all along (in addition to being something larger than a size 2, having a high level of education, and something vaguely resembling standards)?
You’re right, Catherine. That wasn’t fair, on my part. I should’ve been more specific. I actually love it when women email me first. It’s awesome, and I wish it happened more. And truthfully, if a cool girl writes me before I contact her then I remember it. It’s a check in the plus category that endures.
BUT, in my experience, the vast majority of the women who email me first are Capital C Crazy. I wish they weren’t, but nine times out of ten I rush to delete them so their nutiness doesn’t infect my inbox.
So I shouldn’t say that sending the first email makes a woman crazy, just that it’s often the choice of the crazy women.
It’s alright, it’s not you…I suspect that this may be a widely held belief and it’s maddeningly frustrating. Same as in real life–strike up a conversation with a guy in public (even with no intention of flirting, just chatting) and suddenly you’re “too into” him to be worth his time.
Meanwhile, the only men left single at this age (late 20s on) appear to be so because (a) they’re completely socially inept and therefore can’t make a first move (b) they’re shallow and/or have impossible standards and are holding out for a brain surgeon supermodel (as long as she doesn’t make more money than him) and therefore won’t make a first move. Rough stuff.
What if you just constantly met short guys online? What does that mean? That’s one huge reason why I stopped online dating. They were all short and lied about it. But eventually, I going to find out you’re fucking 5’6″ and not 5’8″. And maybe that makes me shallow, but we all have our dealbreakers. Can’t do short. Also can’t do pointy shoes. No and no.
…Also can’t do skull jewelry. But unfortunately, I learned this through experience.
Okay, I’ve been an online dater for several years (um, yes, that was painful to admit). I do not take the experience too seriously…as most of the men online are exactly as you write about. I get it all. Nine out of ten are just not for me online. And, I would fill up pages telling you all of my nightmare dating stories; however, I have a major complaint amongst ALL of the dates I have where I’ve experienced these type.
Guy emails me, seems nice, wants a LTR, desires honest women, he’s great, educated, family oriented…all the right things…(red flags I’m learning) … then, we meet. Date is going great…then, no he doesn’t? Oh, but he does…out of the blue I will be asked what my favorite sexual position is, or would I like to come back to his place…ect…ect…right? Okay, got it, I know what it’s all about…a lil bit of booty, stompin’ in the sheets. However, I’m sooooo tired of meeting guys who gargle how much they want a nice girl…only to end up wanting a piece. I am an attactive gal…not full of myself, but certainly not giving up myself to garbage I find online. Not saying this isn’t in the real world – I know it is.
I think online dating is like playing the lottery. I think there are success stories out there…but they are far and few between.
I think it’s a great way for people to connect with one another; but, believing the love of our lives exist online is a fantasy for most. Don’t take it too seriously or literally, because you will only get hurt. A tip of the glass to those who succeed with this strange way of meeting. But, for me, the painful blind dates are almost too much LOL and I LOVE LOVE LOVE the story of playing the bar game of “who’s on an online date” because I can ASSURE you…I was one of those people looking awkard as I sat painfully trying to “hang in there” after meeting a man online that was untruthful or not the same person he was in from his profile.
Good luck!