My Guide to Having Good Online Dates Part 1: Photos

I Don’t Go On Bad Online Dates, Neither Should You

In life you often have to fail at something a number of times before you become good at it. Online dating is not exempt from this notion. The more you know and have experience with it the better your online dating experience will become.

 When I first started online dating all my dates were bad. Granted, I was going on dates to literally just get comfortable with the experience of interacting with a woman in a one-on-one situation. After a few weeks of going on dates without really screening profiles well I decided I need to come up with a game plan. Most of the dates I went on sucked and red flags that I should have picked up on in their profiles I didn’t. Questions I could of asked on the phone or email prior to meeting I didn't ask. And because of those things I got burnt. Early on I often went on bad dates with women that I had no chemistry with and I wasn't attracted to. Something needed to change. A game plan had to be put in place to avoid the awkwardness of sitting through a bad date.

  My Guide to Having Good Online Dates Part 1: Photos

 (Note* each individual has their own unique set of wants and needs that are important to them. THESE ARE MINE OWN. Your job is to figure out your own wants and needs. Find out what kind of person you want to be with and narrow down the top personality traits and physical characteristics that you must have and go from there. I would advise to not obsess over your lists of wants and needs though. Use them as a guideline for the filtration process of going through the numerous online dating profiles. Having a game plan can save you from going on bad online dates, but being too picky can prevent you from seeing someone that might pleasantly surprise you. There needs to be a happy medium between the 2 to have success in online dating.)

 Part 1: Photos

Physical attraction is key. Anyone who says attraction isn’t first on their list is usually lying to themselves. The default profile pictures are what catches our eye first as we scan through hundreds of online dating profiles. When I search though the pictures of someone’s profile, I have my guideline rules that these pictures need to fall under or I will not proceed with communicating or ever come close to going on a date.

For starters, she needs to have at least 6-10 photo’s. I know some online dating websites only let you upload 6. Not sure why this is the case. A site like Match.com lets members upload up to 25. Do you need to have 25 pictures? No, but I can get a better idea of what you look like with more pictures. More evidence leads to quicker conclusions. 

The photos can’t be all glamour shots, convenient angles or from some special “I’m all dressed up event” such as a wedding. I want to know what you look like on a normal day. While she may look incredible in these wedding pictures or black and white photos, it’s probably not a great barometer to determine an accurate representation of what she really looks like. If all her pictures are from one dressed up event or glamour shots I’d red flag that profile in a heartbeat. If you are still interested in this person by all means message them and ask them for more pictures. You can even say something like “These photos are great but, I want to know what you look like on a typical Friday night.” She should have no problem with this. If she does have a problem then I’d move on. Boom. Done. 4th down, bring in the punter.

You don’t want to waste your time with women who are being deceptive in their photos. It will only lead to you going on date with someone you’re not attracted to and like most men, paying for a meal for someone who you have no intentions of ever seeing again. Remember, 50% of women post photos on online dating sites that are deemed misrepresentations of what they truly look like when you meet them face-to-face. They’re masters at this. It’s you job to do your homework and call them out on it when you think something is fishy with their pictures. If you come away from a profile and say to yourself “I’m not really sure what she looks like still,” then you need to ask for more pictures. It’s only complicated if you make it. The times I went on dates with women I ended up not being attracted to were due to the fact I didn't follow these guidelines.

It’s 2012, Everyone below the age of 60 has no reason to not have an abundance of digital photo’s at their disposal on their computer/smartphones . If they’re reluctant to show more photos you should be reluctant to date them. Let's not be a hypocrite here either. If you are going to have these photograph requests make sure you are representing yourself in an accurate manner with plenty of pictures. You'll have a higher success rate if you practice what you preach.

Part 2: Facebook for Fact Checking Your Potential Date

Tough Love: Women, The Top 3 Things That Turn Men Away From Your Online Dating Profile

3.) Listing Your Demands/Pet Peeves/Dislikes of How Men Treat You Online

Example from a real profile on Plenty of Fish (Yes, this is from a real profile. Verbatim)

Is it too much to ask ... I want a normal boyfriend. 

No.. I will not meet you for s*x 
No.. I do not want to meet you and your girlfriend 
No.. I am not interested in what you 'have' and what 'size' it is 
No..I do not care what kind of car that you drive 
No.. I will not respond to you if you do not have a pic or will not send me one 

.. And lastly If I do not respond to one of your 22 messages...it is safe to say I am not interested. To the above ... 'Kick Bricks' .. And/or 'Rocks' 

This is an instant turn off. I usually see this kinda thing from the more attractive women on online dating sites. The get bombarded with emails and notifications from guys loathing over them. Chill out honey. We get that you are annoyed with sooo many guys chasing after you. Oh poor you. But sorry, we don’t need to hear any of this. We understand that busted, creepy guys are hitting on you cause that’s just what guys do. Spare us the list of your no’s and give us a list of your yes’s. It’s more enjoyable to read and will not make you come off like a ____ (fill in the blank)

There's no need to remind us how sexually driven and douchey the male race can be. We have these thoughts everyday, just not all of us actually come out and say them to you.

2.) "Convenient" Angles/Lighting in Your Pictures 

Women take a ton of pictures these days so it shouldn’t be too much of a surprise of how crafty they can be about which pictures they chose to post in their profiles. They can be very deceptive on how they present themselves. Guys come away from a profile thinking they look like someone else. Don’t believe me?

In 2009 authors Jeffery Hancock and Catalina Toma did a study that focused on the accuracy of photos displayed in online dating sites. The authors had current online dating participants come in person and allow the researchers to take a real time photo. That photo was then matched up next to their current dating profiles. Independent coders were then asked to judge the accuracy of the online dating profile pictures compared to the real-time photo. The coders discovered that 14.8 percent of male photographs were deemed inaccurate, while 48.1 percent of female photographs were rated inaccurate when compared to their real-time photo. The results showed women are three times as likely to have discrepancies in online dating photos than men. The authors attributed the large number of female discrepancies to the fact that men put more emphasis on a woman’s looks when searching for a potential date. The women are dealing with the pressures of living up to a desired self.

While the pressures of living up to the physical desires of what men want can be strong, women have to resist the urge. It will just lead to bad dates. Just listen to Tyler who I interviewed while running online dating focus groups at Rutgers.

“I went out with this one girl once, I talked to her and she seemed cool. But it was the same thing. The angels of the pictures, she listed her body type as one thing and she was bigger than that body type. And it’s frustrating to me because I show up and I’m not attracted to her at all. Now I have to feel like the a_ _hole for going through with this date. If she was just up front about it, we wouldn’t have been going through with this whole charade of now being on a date and me not calling you and all that other stuff.”

Ladies, make sure your pictures are an accurate representation of what you truly look like. The only person you're fooling in the long run is yourself.

3.) Cliché’s

 Hey, we are all guilty of using clichés but online dating profiles take it to the next level. Women, how unoriginal can some of you be? If I read the term “Live, Laugh, Love” one more time I am going to stab my eyes out with a pencil. You really think no one else is using this phrase as their headline? As soon as I see that I’m thinking you aren’t witty enough to keep up with me. On a deeper level, the cliché’s don’t give men the ability to start a conversation with you.

Life offline often imitates life online. In other words, men have to initiate the conversation regardless if there's mutual interest expressed or not. So how are men supposed to start a conversation with you if your profile is chalk full of cliché’s?

 “Oh, you like long walks on the beach? Me too! We should go for a walk down on State Beach sometime.”

See? That line is creepy as hell. Every girl is going to think the guy is a psycho because that’s how he started a conversation. Well, what were his alternatives?

“Oh, you like to snuggle up on the couch with a glass of wine under a blanket on Friday nights and watch movies!?  On Thursdays I like to sit on my lazy boy chair, crushing Budlights while I watch the Bruins game and dream about how I can improve my fantasy football team. We should watch TV together sometime.”

Yup, not getting a response back on that one either.

Women, give us something to work with here. Cliché’s are both a turn off and a dead end street to starting a conversation for men. If you are specific about what your interests are we can be specific in our opening statements to you and not throw the dreaded cliches back at you.

OkCupid’s GPS Online Dating APP Is The Greatest Thing to Ever Hit The Dating Scene

Over and over again in online dating profiles you will see people describe themselves using the superlatives “spontaneous” and “outgoing.” Well, those superlatives are going to be tested to the extreme with OkCupid’s new GPS activated Locals feature.

The locals feature is describe in more detail in this great article by Brooke Lea Foster of the Boston Globe. The APP allows OkCupid members to see other users who are in their general proximity using the GPS tracking system on your smartphone. Members can also post a broadcast suggesting meeting in a particular location or sending out a more general invite to anyone who is in the area. Other users can then respond to that broadcast and you then have the ability to accept or decline the offer. If you accept someone’s request to meet you, you can then private message them in more detail as to the location you are looking to meet. I also like to mention that this service is FREE! (the locals feature does not give out your exact location or use a map as a visual guide, that would be too invasive)

Now many of you are probably sitting there saying “oh geeze, I don’t know about this. Like, what if the person ends up being a weirdo?” My response would be simple. Look the profile over first, if it interests you then proceed by responding back to them and meet up. Wait, is that too spontaneous for you? Well, didn’t you put that in your profile? Come on! I thought you said you were outgoing and adventurous. Time to put your money where your mouth is.

In all seriousness though, I think this Locals feature is tremendous. For someone such as myself that is outgoing and quick witted, its right up my alley. I don’t need 3 weeks to simmer over whether or not I care about all the cliché’s you posted in your profile. If I’m attracted to your pictures and you seem like you can handle my wittiness I’m game. That’s it.

Can you imagine the power and application like this can have on the dating world in a city like Boston? Say you get out of the Bruins game and you’re having a few drinks at the Harp. You want to stay out late but your 2 buddies have to go home because they had a couple of mistake babies in '08 and wife/girlfriend they need to go home too, but you want to stay out cause you’re Boston's most eligible bachelor. Well, before your bros leave you whip out your cell phone and see what women are in your area. In under 30 seconds you find out there is a great girl who intrigues you and she just posted that she's interested in getting drinks with someone 15 minutes from now. Your respond to her, she accepts and you have a date set up just like that.

It’s a beautiful thing really. That is, if you're “spontaneous” enough to venture out of your comfort zone.

Practice Makes Perfect: Why In The Hell at Age 30 Do I Already Have 8 Years of Online Dating Experience?

So I'm sure some of you may be wondering why at 30 years-old do I have 8 years of personal online dating experience? I mean that's just not normal. I started before people were really comfortable with presenting themselves online with websites like MySpace and Facebook. My interest and later success with online dating didn't just happen overnight. I actually started using online dating because I had no clue how to act around women when I was trying to court them. One event in particular opened my eyes to the point where I realized I needed serious help.  Two years ago I wrote about this event. So rather than reinvent the wheel, here it is in its entirety. The night that changed my life.

Don't Just Stand There, Bust a Move

The year was 2002, I was 22 years-old and had not been single since I was 18. While most guys my age spent their late teen years frolicking around college campuses I was in a committed relationship. I was entirely new to whole dating scene, little did I know I had no idea what I was doing.

Around this time of my life my buddies and I frequently went to Providence, RI at this bar called The Fish Company. It was a typical loud, dark bar with a dance floor and DJ and also a seated area of to the side to just hangout and talk. We had happened to come here a few weeks in a row and there was a particular bartender that could not take my eyes off of. She was about 5’7, tan, had blue eyes, long black hair and body of a swimsuit model. She was walking around the room taking drink orders from people. She came by my group of friends a few times and by the second time she came around I couldn’t take it anymore.

I leaned over to my cousin Joe and I said, “hey, I’m gonna go talk to that bartender.” To which he replied, “yeah dude, no way you do it. You are going to puss out big time!” I told Joey to f*ck off. But, the longer I stood there more I realized he was probably right. There's no way this chick is going to be interested in me anyway. However, Joey called me a pussy every ten minutes that passed that I didn't approach her. So, just before last call I made my move…



I can remember as I approached her my heart was practically beating out of my chest, my hands were clammy as hell and I still had no idea what I was going to say. Every step I took toward her increased the crippling anxiety that I felt. I stopped right next to her just as she was finishing up with a customer. She looks at me and just before I opened my mouth I remembered being so nervous that I could barely get the words out. “Hey, do you want to grab dinner sometime?” (I know, brutal) She looks at me and says. “Um… Sorry… but, I have a boyfriend.” Like a little bitch I stood there and then asked her about her relationship. Not only did I crash and burn, but I made myself look like a complete idiot.

I walked back over to Joey shaking my head. “How did it go?” I paused for a few seconds to find my balls that I had dropped at the scene of the crime and then I said, “dude, I have no friggin clue what the hell I am doing. I’m 22 years-old, I have been single for 5 months and I have no Idea how to talk to a woman that I just met for the first time.” Joe replies, “Well, at least you went over there.” Nice bro, thanks for the support.

As we drove home from the bar was thinking to myself this being single thing is complicated as fuck. I kept asking myself the same question over and over again. Why do guys always have to make the first move? What do I even say to a girl when I first meet her? How do I know when to a girl is interested in me? Do girls even find me attractive?

As you can see my head was spinning. Being a single guy trying to get into the dating game with not a lot of experience can be a scary thing. There was one final question I asked myself. “Is there any way I can practice going on dates to figure out what the hell I am doing?” Sounds like a pretty screwed up proposal I was asking myself. To my surprise the answer to that question was yes.

The next morning I woke up, set up a profile on Match.com and began to search for someone to go on a date with me... 8 years later? Well, I'll just say practice makes perfect.

Yes, I Do Online Dating

The faces people make at me when I tell them I do online dating is mind boggling to me. They scrunch up their nose, crinkle their inner eye brows looking like they just ate and handful of sour patch kids and say, “you do online dating? Why would you want to do that?” Yes my people stuck in the 19th century, I do online dating. I mean, why wouldn't I?

I can literally sit at my house on a Wednesday night and pick up chicks by clicking a mouse. Why Joe Blow spends $80 at the bar I have my feet propped up on a couch watching the Sox game setting up a date for the weekend for free in my sweatpants. What guy in their right mind wouldn’t sign up for that? You can simultaneously watch Big Papi hit home runs and flirt with Jenny_617 from Quincy all from the comfort of your own home. I still don’t understand how some single people think online dating is taboo.

“Well, aren’t there a lot of strange people online that lie in their profiles?” I hate to break it to ya, but that’s life. You don’t think there are a bunch of strange people chilling at any bar or establishment that you try to meet other singles at? You come across just as many “strange” or “weird” people online than you would come across in public.

Single people out there, stop using the excuse that there are creepers online for your reason to not embrace the 21st century style of dating. Online dating is here for good and it’s not going anywhere anytime soon. I suggest you get with the times and join the world of online dating. You can meet other single people you normally would never cross paths with. Who knows, one of those people you meet could be the person you spend the rest of your life with. I wouldn’t let a few odd balls online prevent you from having a successful single life. In later blogs we’ll talk about how to avoid these people and not go on any bad dates. Until then, throw on your sweatpants turn on the tv and grab your mouse. It’s time to find a date.