The Self Portrait Picture Delimma

FACT: I have lived under a social rock for 18 years with very boring social life.

FACT: As news of my divorce begins to spread, women and their friends will check me out on Facebook, Linked-In, and any other available sites, including okCupid soon.

FACT: A public image makeover is in order in order to promote interests of eligible women.

FACT: Pictures are the #1 factor in garnering favorable initial impressions.

FACT: As a father, I am the one behind the camera 99.9% of the time. Consequently I do not have a good collection of suitable pictures since I typically photograph other people.

FACT: Selfies are gay. Cool profile pictures should present image of me doing active, interesting things. It should give the impression the picture was taken by other people in a candid moment that is representative of my real life.

PROBLEM: In the next 22 days, how do I acquire a collection of pictures suitable for public image makeover, that appear to be active and candid, even if the setting has to be orchestrated?

SOLUTION: ???????

Definitely not the public image I am trying to promote.


Upgrading pictures is something I have been thinking about for a while and have been working on ineffectively. I actually have a friend (code named Debbie ) who has the same dilemma. I have been working on upgrading her public image as well (since she needs to get her ass out, date more, and forget about this dude she has tunnel vision for.) I have already come to the conclusion that this needs to be done–the sooner the better.

Here are the things I have already accepted I am going to have to do:

  • Moving forward, I am going to have to have to shamelessly ask Debbie and other wingmen to take a pictures me so I can be included in pictures.
  • Short term, I am going to have to use a tripod and orchestrate some poses that don’t look like they are fake, selfie, cheesy poses. (I just threw up in my mouth a little typing that.)
  • Moving forward, I am going to have to do real stuff that create genuine photo ops.

This is the look I am trying to avoid at all cost.

I know WHAT I want to do, I just don’t know HOW to do it. As I mentioned, previous attempts have been ineffective. I have to be realistic here. I am not going to look like Leslie Carter at Bucket List. She is a bonafide world traveling badass adventurer. I am not at her level. I am, however, a hell of a lot more interesting than my current picture  collection would lead one to believe.

So what should I do? How do I go about pulling this image makeover off? Become Awesome and It’s Not a Match — I’m looking to you. I’m the rookie and you have more experience in this online dating realm than me. What are picture mistakes to avoid? What poses works well for dudes? What kinds of pictures should I take of Debbie to help her? How to take a selfie without it looking like a selfie? How do I get a wingman to not be paralyzed by fear and uncomortableness when I hand him or her my camera and tell them that I want them to take a picture of me? How can I do that without coming across as a rude, self-centered bastard?

14 thoughts on “The Self Portrait Picture Delimma

  1. Photoshop?! Pull gymnastic poses against a plain white wall and then cut yourself in to all kinds of exciting scenes – be a pirate adventuring media mogul who hangs with Obama!!
    Otherwise – can’t you and codename Debbie just get freaky and solve both your dilemmas!

  2. Amazing article and guys can relate more than girls probably can. I Don’t have two many great shots, barring weddings or parties. I’m generally the photographer when it comes to most events and I prefer taking pictures because others simply mess it up or it’s nowhere as good as it should be. When I do get one taken? I’m either tired or I just look sloppy. Either ways, the self-portrait-natural-act thing is a tough, tough realm to delve in. Best of luck 😛

    • Thanks for compliment Nickerson. For me, the problem isn’t just the novice photographer not taking the shot right–I am a fairly shitty subject too. It is such an uncomfortable situation that my smiles look painful. To catch a genuine smile on me the shot has to almost be candid where I don’t know it is being taken.

      Women won’t understand this, but handing your buddy a camera and asking them to take a picture of me is a gay feeling. I would pretty much have to sleep with a man to feel in order to feel any gayer than I do asking my beer guzzling/chicken wing eating/married for 20 years friend to take my picture. It is awkward.

      • I can relate and buddies don’t generally do that. When I hangout with my friends, we’d do a group shots, us hanging together but a solo shot? never happening. You won’t go upto your buddy and ask him to take a profile picture-worthy photograph. If it’s a self shot? again, It gets a little gay, standing there, flashing the camera around trying to look cool. So yes, its a dilemma. Probably the only good shots of me are when I’m not conscious and when people force me to get a picture clicked. Generally my female counterparts or cousins. 😛

      • Well, I do feel better knowing someone else feels my pain. It is a necessary evil though. That is the way the online dating game is played. And, really, with social networking being what it is, you have to play the game with traditional dates too. Everybody cyberstalks. Period.

  3. Method: Get stoned or mildly tipsy with a genuine buddy, a soulmate of sorts, of either gender. Play loud music. Ask said buddy to shoot a gazillion pictures. Change décors. You can do it. I did and I’m a nut. My best pictures were taken at the foot of my bed, over the course of one week-end. We took 20,000 pictures. Trust that (i) you will get very tired of your face and (ii) something aesthetically positive will come out of this exercise. You have to make it fun, perhaps moderately silly, even. The fun itself is the photo op, I think, as this is where you will shine and show your true colors, if that doesn’t sound too “gay”. As a girl, I find rock climbing or trekking in the Himalaya pictures and so forth incredibly boring.

    Break a leg! (I’m pretty sure she’ll find you even if you personally think your pictures suck).

  4. I have great photos on my profile, and it’s because I am shameless about getting friends to take photos of me doing interesting things. When I first got back on to dating sites this spring, I enlisted a good guy friend of mine to do a photo shoot at the beach. I got girlfriends to take pictures of me dressed up. I made sure that if I was out kayaking or sailing, that I got pictures. All in service of the dating profile. The truth is that a good picture garners attention, so it’s worth swallowing your pride and posing. And please, no half naked pictures, no pictures of you lying in your bed, no bathroom mirror photos. Ever!

    Here’s a link to a post I wrote about getting my profile up:

  5. If it involves a mirror, it’s a no no. If you look really good one day after getting ready and think, dayum no one is going to see this and I look HOT… take a self portrait but don’t look at the camera eye. Makes it look more candid. Then crop out the tell tale part of your arm that got in the pic. If you are out with a group and they snap pics, make sure you don’t stand too close to the other people so you can crop yourself. Being a man I doubt you will snuggle in anyhoo. And don’t stand so far away you look too cool for school and piss off your buddies.
    And try to get shots in different outfits, casual – suit-sweatshirt- so on. So you look well-rounded and not like that one look is all you can work. Good luck!

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