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5 Stages of How to Lose a Guy (I Met Online) in 10 Days

In a modern-daymoment, I went undercover on five popular dating sites as a reporter. I told myself I'd be just be like a modern-day Carrie equipped with an iPhone and dating apps in hand. Harmless, really...
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I'm 27/F/Manhattan, and after doing a little undercover experiment for Cupid on PC MAG, I'm in a jam and I can't help but wonder.... what would Kate Hudson do?

In a modern-day How to Lose a Guy in 10 Days moment (and yes, that movie is over 10 years old now), I went undercover on five popular dating sites as a reporter. Harmless, I thought. I told myself I have a real online dating profile, so this isn't a big deal. I'll just be writing about my life. I'll just be like a modern-day Carrie equipped with iPhone and dating apps in hand. Well, yes and no.

1. The Masquerade Phase


(source: Tumblr)The good part about "fake" dating is you let go of the outcome. As someone ridden with bouts of anxiety, fake online dating was like Xanax on steroids for social situations. I went on these sites with little shame or reserve. I flirted boldly and approached interactions from a fun-hearted, free-spirited point of view.

2. The Carefree Phase


(source: Tumblr)
And I carried this centered confidence/arrogant armor with me to my in-person dates. Gone were the 30-minute-prior, find-me-any-reason-to-cancel nerves, obsession about my hair and the video montages of horrible 'what-if' scenarios playing through my mind. If I got rejected, it wasn't a rejection of me; it was a rejection of the fake me. So what do I have to lose?

I figured I could be whoever I wanted and the worst case scenario is I have an AMAZING story -- the reporter angle running strong as a mental backdrop. And because I could be anyone I wanted, I became confident, engaging and amazingly, my wit shined through like never before.

3. The Uh-Oh Phase


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I had fun and in true meet-cute fashion (go figure), I ended up meeting someone I started to -- dare I say -- maybe have an interest in. Someone I have fun with, who is polite and kind. Oh, crap... And dammit. Lo and behold, I found myself in a little pickle.

4. The Rationalization Phase


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So what's the solution? What's the moral thing to do? My Catholic school guilt weighed heavily on me for keeping this secret.

For absolution, I turned to the thinking I know best: I was innocent until proven guilty. In true daughter-of-a-lawyer-fashion, I begin to spin and rationalize the hell out of the situation.

1. I already wrote my review, so I kept my journalistic integrity.
2. The dating site review will probably never be found anyways.
3. I "technically" am not "lying," because I fully disclosed that I'm an editor for a tech company, which does reviews... (right?)

5. The Honesty Phase

(source: Fanpop)

OK, yes, I know, I borderline lied by omission, and I know I have to suck it up and be honest now. But is it that big of a deal? We shall see...

Admittedly, I ventured into this ordeal with more than a little skepticism about online dating. I have no doubt it is the future of dating and couldn't agree more with Wired's 2002 prediction that come 2022, "the idea that someone looking for love won't look for it online will be silly." Still, I approached the sites with an 'I'm above all this' attitude. I reasoned that anyone who was a catch, both inside and out, would have no reason to be on an online dating site. And as a society, I think we're still at a problematic stage where online dating as a last resort is still very much the status quo.


Online dating taught me to push through the awkwardness and take responsibility to what (or who) makes me happy -- by meeting people in-person. Texting is not dating, and a dating site isn't going to make you fall in love; that's not what you're paying for. Dating sites simply make it easier to make initial contact, but makes the process from the online world to the offline one an even bigger hurdle to jump.

In such a blunt, no-holds-barred time, I find it odd that in dating, we're easy when it comes to interacting with our thumb -- like, comment, wink, chat, message and text -- but reserved when to comes to meeting in person.

My Online Dating Tips, from Experience:

Tips from my review and experiment:

  • Note her answer to 'The first people notice about me...' question and be sure to compliment her on something different in person.
  • Look to see if she mentions her career in the self-summary and the 'what I'm doing with my life...' box. If she does so, avoid that topic and ask about something else she mentions. Chances are, her work consumes enough of her life and asking her to talk about it won't help you stand out from the crowd.
  • Tips from my
    and experiment:
    • You have her industry, but may not have her exact line of work. If she doesn't note it elsewhere on her profile, ask her for specifics of what she does beyond her title, such as what does she do on a daily basis, how she did she get into her field, etc.
  • Look at her 'In her own words...' section and read the last sentence in that section. What she writes here is the last thing she wants you to read about and probably what she wants to emphasize most. Find a way to spin it into a question or two.
  • Tips from my review and experiment:

    Google the name of the university she went to. This can give you an easy in for some playful college rivalry teasing and even better, tells you what state she lived in for a least a few years.

    • Use 'The one thing I'm most passionate about...' question and probe more details about it. Chances are she has more to say than what she could fit into that answer box.