You're a busy guy. You have a lot going for you and a lot you have to do—work, friends, family, the dog, the gym and everything in between. With the progression of the digital age, our lives get busier and busier which makes finding a relationship difficult.

The digital world has a way of righting itself and to make up for lack of relationship time, the electronic age has designed online dating. What used to take a certain number of outings in social situations, the person you're interested in also being available and interested and a good dose of luck can now be done from the comfort of your living room.

With so many apps and sites out there touting they're the company that will help you find true love—or at least a date to your brother's wedding in six months—how do you find the right fit for you? Once you sign up, where do you go from there? We got you man.

Why Is Dating So Hard?

help sign

It's no secret most everyone has had trouble dating in the last five years to ten years—it's hard. But why?

We Want Perfection

You have too many choices. It's like when you're shopping for a pair of running shoes. Depending on the store, you may have upwards of a hundred options. It's the rare person who walks in, looks in their price range and buys the first pair that fits well. Most of us try on endless pairs, certain there's one better than the great pair we just tried on.

We do the same with people. The internet, various dating apps, social media and other sites have opened the world up to us. That means you may be in a great relationship but you're certain you can find someone hotter, smarter, funnier—whatever. Most women you date feel the same way you do. People walk away from potential love after one or two dates because someone better may come along.

Nobody Looks Up Anymore

When's the last time you sat in a waiting room, alone in a restaurant, on a bench or anywhere you have a bit of free time and just spent it looking up, making eye contact and enjoying your surroundings? Right—that's what we thought.

In days gone by—like the 90s and 00s—people met other people in places like that. Strangers would strike up conversations in line at the grocery store, waiting rooms and at the bar waiting for friends to show up. This is a big reason people think other people are aloof and unavailable—they're actually in a pretty serious relationship with their phone.

Try going an entire day, not getting on your phone while you're away from home, other than necessary phone calls—like with a voice on the other end. If you find it difficult, you're in love with your phone too. We're always available to other people and the world is always at our beck and call—this leads to aggravating ignorance of the physical people around us.

Made Up Rules

Seriously—who made all these stupid rules? Don't text for three days? Why—for the love of God, why? If you want to text a girl you just went on a date with, do it—do it four seconds after the date is over. Whatever. If she's a good match for you, she'll love it because she was just about to text you too.

Somewhere along the way we, as a dating app society, stopped doing what we felt like doing and started doing the opposite. There are “rules” saying that the more you like a girl, the less interested you should seem because you're not wanting her will make her want you more. Huh? Call if you want, text if you want—just be respectful and you have nothing to worry about.

Girls are hip to this game, by the way. If you wait three days, there's a good chance she spotted your game and moved on. The game won, son.

Traditional Dating vs. Online Dating—Who Wins?

hand shake

Online dating—successful online dating—eventually turns into traditional dating. Here's the thing about the traditional way to meet people—you need to be places your potential partner may be. If you don't go to social events, bars, sporting events, concerts, etc. you may not run across someone who catches your eye.

If you're not loving the idea of dating someone you work with or in your immediate circle of friends—nobody is Ross and Rachel—then you'll need to venture out. You're not the only one with your head down on your phone. Most of the women you may make eye contact with have their heads down too. Online dating gives people a way to meet other single people looking for a relationship—it's like one big singles night at a club.

Commuting gets in the way of just walking into love. In the olden days, people met and married people in their neighborhood. There were community BBQs and get-togethers and all the neighbors knew each other. So many people have extended commutes, there's less opportunity to meet either a woman you'd like to date or someone who knows a woman you'd like.

Online Dating

  • Makes meeting people easy and convenient
  • You can check your account 24 hours a day
  • You're able to vet people before you engage in meaningful conversation
  • Tools offered by a site can be a built-in matchmaker
  • If one beginning doesn't work, you don't have to start all over

Traditional Dating

man with flowers behind his back
  • Meeting new people is hard for a variety of reasons
  • Meeting people has limiting time constraints
  • It may put you in awkward position of wanting to stop a conversation you started
  • Each date is a roll of the dice
  • Starting and re-starting is time-consuming when you're already busy

Dating or Hooking Up?

There's plenty of both to go around If you're looking to hook up, there's an app for that. Hoping for something a little more serious? There's an app for that too.

Hookup Apps

  • DOWN Dating—this app uses your FB friends and friends of friends to create matches—you can let them know if you want to get down and get out
  • Happn—this lets you know who you “happen” to cross paths with during your day—you only get matched with a person who says she's interested in you too
  • Casualx—wanna guess what the x stands for? This is for straight-up sex, swinging, friends with benefits, etc.
  • Feeld—this is strictly for people looking for a threesome. It works like Tinder so you can find your preferred configuration
  • Tinder—the OG of hookup apps. It's straightforward and everyone is on it—that means everyone is on it and you're going to run across familiar faces as someone you know scrolls past your face
  • Whiplr—an app for fetishes—you get hooked up with people with like-minded, um, fetishers


Dating Apps

  • PlentyofFish (POF)—this site offers a personality test to find better matches, browse other profiles anonymously, chat and email for free—this is a free site but offers upgrades for a fee
  • OkCupid—matches you according to answers on their quizzes, free chat and messaging and specify the relationship type you're seeking—free with upgrades available for a fee
  •—also an OG, Match uses keywords to find matches for you. Users can “wink” at each other for free, but you have to pay to communicate with each other
  • Zoosk—over 50 million people are on this site. Zoosk requires users to upload a photo—like Match users can browse and wink for free but have to pay to actually communicate
  • eHarmony—one of the pricier sites—eHarmony has more questions than any other site in an attempt to find you a great match
  •—users take a personality test and are matched according to answers. This site also makes suggestions for dates based on your collective answers—this is subscription based so you have to pay a fee to communicate
  • Our Time—this site is for people 50 and over looking for a long-term relationship. Users need to buy a subscription to communicate with each other


Free vs. Paid Sites

Free sites are a great way to get your feet wet if you've never online dated before. You can get a feel for profiles and what it's like to chat online. Here's the thing about free sites, you're more likely to get impulse online daters—someone just had a fight with her boyfriend and created a profile. You chat it up with her, make plans for the next day but that just so happens to be the day she gets back with Mr. Wonderful.

People who are more serious tend to join the paid sites. This isn't universally true but you're playing the odds. If someone is willing to pony up between $15 and $50 a month is tired of the single life and is hoping the digital age will help them find love.

Why You Should Give It a Shot

The first thing you have to do is get any stigmas about online dating out of your mind. Every new form of dating came with its own set of eye rollers—marrying your high school sweetheart, meeting your spouse at a bar, being set up on a blind date, dating at work—all came with their own set of stigmas.

There is no wrong way to meet someone—the important thing is being able to meet someone when you're ready. Think about our reasons for joining online dating:

  • You have the chance to meet all kinds of people you wouldn't normally have a chance to
  • You get to filter out poor matches and not waste time
  • When you set up your profile, think about and articulate what you're looking for—clarifying what you want
  • There's less pressure to go on a date—you can do plenty of communicating before you meet for coffee
  • If you're worried about fear of rejection, these sites will give you a wider pool of potential matches
  • You get to know a person before the first date—you'll have more commonalities to talk about when you actually meet face to face
  • What if “the one” is waiting for you to join? Cheesy? Sure. Potentially realistic? Yep

Pros and Cons of Online Dating

Nothing is without its up side and down side. Even pizza and beer have a downside—we don't remember what it is, but we're sure it's there. It's good to go into everything with your eyes wide open.


  • 1 in 2 people have tried online dating so you're in good company. There's research to show 1 in 5 relationships starts online
  • Dating sites use your information to pair you with the best algorithmic match available—that's better than your buddies' girlfriend will do
  • Great people are out there and you may never come across them in your everyday life, but you can online
  • If someone gets a little crazy with you online, the site will have tools to help you block and report weirdos—we want that tool in real life


  • There are a lot of people on these sites and the numbers can be overwhelming
  • No matching software is perfect and people lie on their profiles. Someone who didn't graduate from high school can claim to be a doctor—that's why chatting ahead of time is awesome
  • It's hard to really evaluate chemistry without physical interaction—things may go well and fizzle out when you meet up
  • 63% of marriages started by meeting through a friend so that's still your best bet—we suspect that will change over time

What Site Should I Try?

It's always good to get the feel of online dating by using a free site. You can get an idea of how the whole thing works without ponying up while you're making mistakes, moving slowly and just getting used to all of it. Try a site like Plenty of Fish to get going. It's not a “hook-up” site but you can follow a connection through to a date and who knows—that may be all it takes.

If you're finding the free site to be a little flaky and you want to meet people who are more serious about finding a real relationship, then give or Zoosk a spin. Sign up for just one month to start with. You may find the way they match or how communication works isn't something you want to sign up for over the next six months.

If start in this order, you'll already have a feel for how it works. You will have refined your profile skills, who you do and don't want to communicate with and when you know it's the right time to meet up in person by the time you're spending money.

The Most Important Part—Your Profile

This is the most daunting task of all. You are an entire person with this big full life and long history and now you have to sum that up in about three paragraphs. Welp—that's going to be tough. It doesn't have to be. We're here to help you out—nobody should go at this alone. Sure, you would fight a bear if you had to but online profiles are scary.

The Picture

Do not underestimate the power of your profile picture. You could have just cured cancer, walked on the moon and have a sloth farm in your backyard—doesn't matter if your profile pic is blurry, weird or too posed.

Pick the best picture of you that still looks like you. Yeah, we all have those pictures where the planets aligned, and we look like a young Brad Pitt. As much as you wish you looked like that, it's misleading to post it—go on your first date when the person who shows looks nothing like the pic and you'll know how uncool it is to mislead.

Go for a pic that shows off a great personality trait—casual, formal, laughing, throwing a ball for your dog—whatever it is, make sure your face is clear and make it fairly recent. Going back more than two years or ten pounds isn't a great first impression when you meet. Of course, pic a great one—you don't want to go so overboard at showing the “real” you that you pick a slovenly hangover pic.

Picture Tips

  • Pick a great picture that looks like you
  • Show your personality
  • Make it recent
  • Don't go for overly posed

The Words about You

You need to start with the title or headline of your profile. Ugh—what will make you stand out in a sea of people trying to stand out? Well, what actually makes you stand out in life? Don't be afraid to use that. We know someone who's headline was “Ridiculously funny or funnily ridiculous—you be the judge”. That totally works.

Nobody wants to see a huge wall of text. Break your story into small paragraphs broken down by topic or thought. Don't know what to say? Think about this:

  • Use a conversation starter and a call to action. If you love action movies you can say: I can recite every line of Die Hard in my sleep and most of Jaws while I'm awake—what movie do you know every line of?
  • Keep it positive—talk about what you want, not what you don't want. What qualities get you energized and excited? Talk about that
  • Show them, don't tell them—so many people talk about how funny they are—don't be that guy, just be funny. Whatever adjective you're going to tell them about—funny, smart, sensitive, thoughtful—let it come out in your writing
  • Be honest and genuine—don't spin tales or exaggerate stories
  • Mix it up—cover several topics. Talk about work, family, hobbies, travel, movie and what makes you laugh or cry—maybe just laugh to start with

Information Tips

  • Keep it positive
  • Don't tell, show
  • Use a conversation starter
  • Be your genuine self
  • Mix it up to show your diversity


Take Your Time

This isn't a race. If it takes you a week to get your profile the way you want, good. It would take you a week of dating to get all this information out anyway.

Fill every section out—it will help organize and break down your thoughts. Write a paragraph and walk away. Come back to it 20 minutes later and read it over.

  • Is it getting what you want across?
  • Could you say it in a simpler or better way?
  • Is it honest?
  • Would you want to read more if you saw this?

If it's where you want it to be, then move forward to the next paragraph and continue this process until you've completed your entire thing. Let it sit for a day. Come back, read the whole thing start to finish—you'll catch typos, boring spots or repetition. You're good to go!

It's in the Chat

This can be nerve-wracking—you've found a girl you want to chat up so you're on the page to send her a message and…you stare at the screen. How do you start? Hello. Nah, you can do better than that. Use these tips:

  • Use her name—"Hey Julie” is better than “Hey” any day of the week
  • Mention something about her profile—“How cool is it that you've been to Bali?” It shows you read her stuff and not just glanced at her pic
  • Ask her something so she is comfortable writing back—“What's your dream vacation?” Ask something to keep her talking about the info that drew you to her in the first place
  • Throw down some feelings—“It looks like we have a lot in common” or “I think we'd really hit it off”. It lets her know you're interested and not waiting for her to make a move

It's a Date!

Well, now you've done it. You've chatted it up and it's time to meet—like in real life. There are definitely best practices to make sure you have a great time or make it out quickly.

Keep It Short and Simple

There's one rule that's never failed us on a first date—meet for coffee. Seriously. If you go to dinner and know within five minutes you don't have chemistry—you're stuck for like an hour and a half and you're out $100. Coffee can be 20 minutes or can linger and turn into dinner if it goes exceptionally well.

Drinks can be good too but limit it to one. Her and your judgment can get questionable after that—remember you want to get to know her and see if there's potential. There's always potential after six drinks.

If she insists on dinner, make up a reason why you only have time for coffee, but you'd really like to meet her. This is just a good way to flush out the off chance she's out for free fancy food. Coffee—it's your friend.

Here's Your Chance

The coffee date is set! You're on your way to true love, man. Here's your chance to leave all those stupid rules we mentioned before at the door. Listen, if you want to play hard to get or disinterested expect her to not be interested.

It's ok to smile, lean in to what she's saying, make eye contact and ask follow-up questions. If you're interested, let her know—If you don't, someone will. Other tips:

  • Don't make her wait—ever
  • Pay for her coffee if she lets you
  • Offer to refill or get her a baked good if it's going well—girls don't want to blurt out they're hungry, get yourself one too so she's not eating alone
  • Don't go into it with an and game in mind—you can decide later if you're going to ask her out again, kiss her—whatever. You'll be in your own head too much if you set a “goal”
  • Don't try to get her to like you—either she will, or she won't. All you can be is yourself
  • Relax, be yourself and enjoy your date. 

More Great Advice

You've done the hard part. Deciding to take the leap into online dating, making your profile, chatted with someone and planned a first date. It usually takes a few dates and lots of chatting before you land a relationship. Use these final tips to increase your chances at success:

  • Be aware she may be freaked out so always offer to meet in a public place—it's safer for you too. You never know.
  • Tell somebody where you're going. It's just a good practice for everyone.
  • Always suggest you meet her there on your first date—you don't where she lives and you don't want to be committed to drive her home if things go sideways
  • Check yourself in the mirror—we know you're busy but make sure your clothes are clean, teeth are brushed, and your hair is washed
  • If your date doesn't look exactly like her picture, be polite. A few extra pounds or different hair color can be overlooked if she's awesome. It's ok to not stay if someone walks in looking like a different species than her picture.
  • Don't chat for weeks before asking for a date—if you like her, be brave
  • Don't send indecent pictures for God's sake unless she's asked for them—you'd be surprised how many D pics she's gotten
  • Don't go on and on in texts after the date about how much you like her—ask her out again!!

Go, Go Find Love

(Designer_start) [insert gif of a fish from Finding Nemo saying “I look at you and I'm…I'm home] (designer_stop)

Well, there you have it. You are one step closer to finding a relationship and having fun in the process—remember like any dating scenario, it should be fun. If you're having fun and she's having fun, why not just have fun together? You got this.