Online dating is hard. And not in the good way.

First of all, yes, I’m admitting to succumbing to the Internet to date. I’m not going to defend my decision to do so farther than stating that I don’t like to meet guys in bars or clubs as they’re only looking for one thing, and with my work and play schedule, it’s hard for me to meet anyone outside of, well, the Internet.

Second of all, it’s hard. Really hard.

Step 1: Creating a profile

How can you accurately sum up your life in categories? My life is not necessarily categorized by “what I’m doing on a Friday night,” or “what I’m really good at,” or even, “my favorite books, movies or food.” Nope. Sorry. There’s more to me than all of that. Not to mention, I have to sound interesting enough for a guy to actually message me. Don’t get me wrong, I’m interesting. But, the fact that I’m 5’3”, only drink occasionally and own a cat might suggest otherwise.

Along with answering these mind-numbing questions, you’re presented with even more of a challenge. You have to choose a photo. Lucky for me, I’m fairly photogenic, but it’s still a crapshoot when trying to pick the perfect one. Do I pick one that’s a little sexy? Then what message is that relaying? Do I pick one of me outdoors? Dressed up? Dressed down? Out? In? Short? Tall? Clothed? Not clothed? AH!

Then the tests they want you to take (you know, in order to increase the ability to match you with someone you might get along with) are absolutely ridiculous.

“Some friends invite you to go camping where there are no showers, no toilets, and no services. The only luxuries would be those you could carry in a pack on your back. Do you go?”

Can someone please tell me how this question will impact my dating life? Thanks.

Step 2: Finding “matches”

Ok, so your profile is set. You’ve taken the dumb quizzes and tried to be as honest as possible in answering the questions. Now what? Well, some dating sites actually attempt to perform some sort of ninja analysis of your answers to the dumb quizzes and find others’ answers to the dumb quizzes and POOF! you’re a match.

Sometimes, these “matches” seem like they might be right on. And others…just…don’t. Like, I’m sorry, but I’m not interested in a 4’11” little man who is an emo poet in his parent’s basement in Timbuktu, California. But! But! But the site says he’s a 97% match! Bologne.

Chivalry is dead

With online dating, there’s no “wait for the boy to make the first move.” I mean, of course, you can wait for them to message you, but with all the profiles to patrol, it’s pretty impossible for the guy you’ve been eyeing to know you’re eyeing and then message you. So, you have a couple options.

You can go out on a limb and message them. What do you say? “Uh, hi. I saw your…achem…profile. Judging by a picture that may or may not be you, I think you might be cute. Also, I think that we both like ice cream. Wanna chat?”


Ok, so you don’t want to send a message. Well, you can give them a high rating (stars) and then let them know that you gave them a high rating and then hope they give you a high rating, too. And if they don’t? Well, then you think you’re LOW-RATED.

Screw the rating. Instead, you can just “wink” at the person you’re cyber-stalking. Because that’s not creepy at all.

Step 3: “You’ve got mail”

Guys will message you. Some of them might even pique your interest. Others, will repulse you. And if you’re really lucky, you’ll get a gem like this one that’ll just make you laugh:

“Holy damm. So I Read you’re jewish,cool. Im 1/4 Jewish. My parents are from Ukraine- Moms is mixed.”

You see, if he actually read my profile, he’d see that I’m a writer. And if he had his head on correctly, maybe he’d take a little extra special care in crafting a message void of glaring grammatical errors. Then again, maybe that’s asking for too much.

Step 4 (not often reached): The first date

You find someone that can spell and looks like they might be interested in similar things, and doesn’t appear to be a serial killer, so you decide to meet in person. All you’ve seen of them is their profile picture (and if you’re good at stalking like I am, you’ve hunted down their Facebook, Twitter, blog, etc.) BUT, all you’ve seen are pictures.

You arrive at the predetermined location. You scan faces, looking for a spark of recognition. You come to the conclusion that he’s not there, when all of a sudden, the scrawniest of scrawny guys perks his little ears up and recognizes you.

“SuperDude49?” you question, hoping he’ll say no and you can just chalk the night up to a blow-off.

“Yep! That’s me! Gosh, you’re gorgeous!”


Bottom line is that photos are deceptive. Like, there’s no way his “Body Type” is “Athletic” unless starving yourself has somehow become a professional sport all of a sudden. And that picture? Yeah, it must have been from 150 years ago, you know, before the potato famine.

Ok, ok, you get past the fact that the guy looks nothing like his picture. (I’m in no way, shape or form superficial). We had great conversations, right? We have so much in common? Well, then you find out that he’s not really a surgeon, he’s more of an insect dissector. He’s not really living in a huge apartment by himself, it’s actually the in-law apartment of his parent’s house. He’s not actually anything he described himself to be.

Step 5: Letting him down…

All right, the date is over (thank God) and you’re thinking, “ok, that wasn’t so bad. But, I’m not interested. I’ll just tell him and then move on!” Well, it’s not that easy, sucker. Why? BECAUSE THE INTERNET IS ENDLESS AND HE CAN AND WILL ALWAYS FIND YOU. Sure, you can block him from your dating profile. Yeah, you can unfollow him on Twitter. Yes, you can unfriend him on Facebook. But he is always lurking and you don’t know where or when he will strike again.


Unfortunately, I don’t see a way around any of these scenarios. And I know, dating (in general, not just online) takes risks. But, I think, at least for a little while, I’m going to try meeting people the “old-fashioned” way. You know, face to face. Or at the very least, blog about my silly online dating experiences. Ugh. I don’t know which is worse.

/end rant.

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  1. Okay. First, I have to say, “Amen” to that entire rant. You know I’m long winded so I’ll be super fast mode.

    1. I’ll send you a link to my profile because I need pointers. I tried to be brutally honest in everything and girls I went out with would meet me and say, “wow it was just like your profile.” so when people do that, you’re just wasting everyone’s time and guys usually are paying so WTF. A girl expects A and you show up as B and you still gotta shell out dough despite the fact she,s screaming, “GETMEOUTOFHERE” (which I found very funny).

    2. Dating in San Francisco is EXCEPTIONALLY CHALLENGING. There are girls like you and guys like me. Don’t read into that, you’ve said it yourself about work and personal time and you blog about your commitment to everything but getting a boyfriend or maybe that changed but I’m just going by your blog. Then there are guys like me. Romantics, workaholics that are in need of something more, that want a romance but can’t devote all of their time to it but, at the same time haven’t been laid in an incredibly long time. Like over a year.

    The answer in SF and most big cities (although New Yorkers that have moved here told me that NYC is dating heaven) is that you’ll have business contacts (a lot of them) and 1 out of 200 contacts is someone you can actually hang out with. 1 out of 500 can be your best friend and if that 1 out of 500 is a girl, then you might have a long term relationship but if either one of you feels the career goals slipping away, it could suddenly end and someone gets hurt.

    What people do is network, hang out and fuck. That’s SF and the fact that SF was historically a gambling, transient gold digging (literally) town with prostitution and then in the 60s-70s it was hippie capital of the world, it’s basically been a liberal, anything goes transient culture which is what we see now in the startup community. were’ all trying to strike it rich but most of us leave broke and full of great stories.

    So…. if you don’t like the smell of weed everywhere and don’t like “hooking up” because it’s been a while and don’t like homeless people then SF isn’t for you. Well, that’s me and it’s why I want to move somewhere else next year and leave sf.

    3. I think Internet dating is a waste. I did it for 2 years after high school and never was happy. I did it for a few months after Laura and had terrible luck. I gave up and haven’t been on a “date” in like 7 months. Wanna know what I did? (maybe it’s different for women)

    I stopped wearing headphones, stopped reading my iPad / iPhone and on my 1.5 hour commute to and from work, I see random girls looking at me, I walk over and start chatting. 1 out of 20 I’ll get a phone number if I feel a connection but I am real about it and I’m talking to a couple of girls that I met randomly.

    Internet dating is harder than just grabbing your balls (i know I’m a d00d) and talking to people who you’re attracted to. That’s the secret and You’ll know by the end of the first date if it’s someone that matches your style, way of life and life goals.


    I’ll keep things you and I have talked about offline there but there are other things I’d like to say that we can cover next time we chat. I have some more stuff to vent about next time we grab coffee. fo realz!

    Not sure what site you’re on but I’ll send ya my profile so you can give me some pointers.


    good post. sorry to totally type too much. *hugz*

    • Wow – definitely some good insight here! We should get together and rant :) I’m not sure if it’s San Francisco or the Internet that’s making it difficult – I’ve only tried online dating out here.

      Thanks for the comment, Adam!

  2. I think dating in SF in general is difficult. With online dating, at least you get a preview… Whether or not the profile really tells you anything about the person, it’s up to you to go and hang out to see. I think it makes it easier for those who don’t approach people on the streets or at bars.

    And even though my current boyfriend and I met in person initially, most of our communication did occur over the web, such as chatting or emailing. That’s no different from texting someone you met the night before at a bar or through a friend. It’s just how we communicate nowadays.

    I went on several dates with a guy through OKCupid. He was nice, but we didn’t really have the chemistry, and he hadn’t lied too much in his profile.

    Good luck! :)

    • That’s how I’ve always looked at it – at least you can see if you have anything in common before you waste your time. But, I guess I just haven’t had the best experiences…

      I completely agree that the web is where we communicate, but at least if you meet someone in person first, you know if there is chemistry or not. If you just talk online first, you don’t have a sense of the “it” factor that’s so important in a budding relationship.

      Thanks for the comment!

  3. First off, love the title.

    Secondly, it seems that everyone has the same complaints about online dating. Wouldn’t you think it would be better since we all know it sucks. We the rational people need to clean it up. We need to be the Rudi Guiliani of online dating. Lauren: online dating :: Rudi: Times Square.

    Thirdly, I think online dating is all about honesty. You have to put your best self out there to try and snare the best possible mate but a lot of people go too far and just straight up lie. No matter that they are a wonderful person, they have gotten off on the wrong foot and started your connection with a lie. And that’s just not cricket.

    Great post, Lauren. Thanks for sharing.

    • I thought you might like the title 😉

      Of course online dating is about honesty – but with the freedom of the Internet, you’re “allowed” to be whoever you want to be. In some cases, that person isn’t really anything like who you really are… That’s the caveat with creating your own depiction of yourself…

      Thanks for the comment, Jeremy!

  4. Gosh you’re gorgeous!

    Ughhh lady – I wish (no, not really, I don’t, but I’ll say I do to make you feel better) I could sympathize. Just keep on’ keepin’ on (god, did I just say that?)… And keep dating online because these stories are FUNNY.

    • My friend Cameron told me that I’m a true writer. (Duh). But why? Because find good in every situation. That good? Is that no matter how bad or awkward or strange the experience is, I think to myself, “Well, at least it’ll make for a good blog post!”

    • Aw shucks. Thanks, Casi!

  5. Oh yes. OH YES. This is exactly how I felt when I was doing online dating.

    I only made it to one first date and I was so nervous and not even at all excited that I told myself, “NOT AGAIN!”


    Sorry for all the yelling.

    • SOMETIMES YELLING IS NECESSARY. Trust me, if I thought anyone would read this post if it was in all CAPS I would have written it that way.

      As soon as I find a better way, I’ll let you know. It’s a jungle out there.


    I cringe when someone asks me if I’m seeing anyone. Because the MINUTE I say no they ask me one of two questions:
    1) Don’t you ever meet anyone at Google? and
    2) Well have you tried online dating?

    1) You’d think! and
    2) YES. BUT I HATED IT. Please don’t make me go back! But it somehow seems like the only way these days? That depresses me.

    So thanks for your amazing post – I felt a little less alone in my frustration. And you NAILED all the reasons I have a hard time with it. Love it!!

    Have an amazing weekend – great to see you the other day 😀

    • SO good to hear I’m not alone in the miserable world of online dating… WHEW!

      I get those two questions, too…

      Q: What about people you work with/are in the same industry?
      A: First, I work with 40 people. That’s it. Second, I don’t really want to date someone that works just as much as I do…we’ll never see each other! All we’d end up doing is Twitter-Dating.

      Q: Well, have you tried online dating?
      A: Yes. HAVE YOU? If you have, then you wouldn’t be asking this dumb question.


      Amazing seeing you, though!!! :)

  7. Ok, Lauren? Sorry but this actually made me laugh. Mainly because I’ve been there, done the same things. Down to pretty much the same outcome … I actually found out later that the profile picture was a younger sister. Ho-hum.

    Thank you, NEEEEEEEEEEEXT!

    • It was supposed to make you laugh! It seems the online dating experience is nearly universal. And it’s all about the “Thank you, NEEEEEXTs :)

  8. Thanks for the post, I enjoyed reading it. I have tried online dating with mixed results; nothing amazing came out of it but it wasn’t a COMPLETE waste of time because I feel like I learned from the experiences.

    Let me preface my comment by saying that I’m in the same boat as you so don’t take this as me handing down condescending judgments from my high horse. I think that the reason some people have difficulty with online dating is the same reason those people have difficulty with non-online dating. Whatever those reasons may be. Internet dating may have changed the process a bit, but people haven’t changed. If you’re the type of person who finds dating to be a grueling process (I’m one of them), then the internet isn’t going to change that. It’s disappointing but I think it’s the truth. So unfortunately I don’t have any answers for you. Sign me up for that list if someone finds the answer. :) Btw, I’m a male in case anyone was wondering, but I think that what I’ve said is true regardless of gender.

    • You’re very right. Dating is still about meeting people in real life, whether you “meet” them online first, it doesn’t matter. I’m glad you enjoyed the post, and can relate.

      Just an update from me — I met a great guy on OKCupid and we just celebrated our 1 year anniversary in December. There are good guys who date online, too :)

      • Wowza… Did not see that coming! Congrats!

  9. It works well for some people, yet not for others.

    Man’s point of view:

    (1) Excess competition: I have to compete with other men, of all ages, some whom are legitimate, the rest are seeking fun in the sun. Let’s look at this for a minute; in the real world, these young bucks or old toads wouldn’t even contemplate approaching a woman who is not in their ideal age / attractiveness range. Online, it’s a whole new ball game. People send out random messages, in the hopes of garnering interest from a woman. The situation becomes difficult, as women I would usually approach are being inundated by dozens of emails, most of which are useless. Thus, process of elimination is even more severe than offline. In other words, it’s easy to get lost in the mess of profiles. Even when a conversation is struck, it’s difficult to maintain contact as he/she may be and likely is, having multiple conversations.

    (2) Nature of online dating: We have pictures, we have profiles, that’s it. There’s no non-verbal communication, i.e. smiles, smirks, flirtation, turrets syndrome? There’s no verbal interaction. Do you even like the woman/man’s voice? Does he/she sound completely illiterate or uneducated? Are they really outgoing, gregarious, or completely shy and/or awkward in person? Do the pictures posted, even resemble the person you’re chatting with? How about the profile, is it embellished, 1/2 truths, or completely false? These are all potential time wasters, resulting in frustration for both men and women.

    (3)Overinflated sense of self: Let’s face it, when someone is inundated by email, that’s going to have a direct effect on their perception of dating value. It’s not representative at all of their true value offline. The result is, even an average looking woman or man is going to start being overly picky online, vastly misrepresenting their dating prowess. In addition, even a completely introverted woman or man is going to feel like the queen/king of the heap, simply from the baiting emails they receive. They become overly picky.

    From a good looking, well educated/employed, funny guy’s point of view, I’ve come across all walks of life online and some that I’ve met, have been a decent match. Others I wouldn’t have anything to do with, had I originally met them in person. Once again, it works well for some people, for others it becomes a time wasting impersonal approach to dating.

    I’d just rather meet the old fashioned way, through friends,coworkers, family members, or extracurricular activities. At least then, you know what you’re getting into, with very little chance of coming across 1/2 truths or worse, flakes or desperados.
    To be blunt, in the real world, you avoid the losers.

    • Absolutely! Online dating isn’t for everyone. I appreciate your thoughtful comment!

  10. I think on line dating is a big scam. I’m a lonely widower and I tried a lot of different sites, It seems like all they want is your money to send a message or chat. one site in particular (CONFIRIO) had a lot of pretty gals that said they liked my profile. But when we chatted I found out most of them were PROSTITUTES or wanted me to send them money to west AFRICA. I think it’s really repulsive that people want to make money off other peoples misery. I’m sorry if I sound negative but I feel hurt that there is not some place out there that is not compassionate to the needs of lonely people. all I want is some female company to chat over a cup of coffee or a date for dinner.

    • I’m sorry you feel that way, Louie! I definitely think online dating is a challenge and has it’s ups and downs. But I do think that success stories come out of it, for whatever reasons. My advice to you would be to keep trying (I know you didn’t ask for my advice, but I felt compelled). Never give up. Get out there and you never know who you’re going to meet. Also, sometimes, it finds you when you least expect it and when you’re not, in fact, looking for it. Best of luck!

  11. Want a date?


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