Oh February, you are a truly loved or truly hated month, depending on your state of coupledom. Whether you call it Valentine’s Day, Singles Awareness Day, or “I’m-pretty-sure-a-pint-is-one-serving-and-nobody-gets-me-like-Liz-Lemon” Day (#NightCheese) you’re probably at least thinking about February 14th.

Maybe the impending arrival of a naked cherub taking aim for your heart with his little baby bow and arrow has made you take the leap into online dating. Maybe (like me) you’ve been dating online for years. Either way, online matching has become big-business and has rapidly lost the stereotypes of a “creepster behind a keyboard in his mother’s basement” and moved into the “driven, urban, professional with a tight schedule” crowd.

When you first plunge in the online dating world however, it can seem a bit overwhelming.

“He winked at me…what does that mean?”
“Should I e-mail her first? How long should it be?”
“Do I sound like an idiot?”
“Are they actually cute or is that picture old?”
“Did I swipe left on my soul mate?”

And round and round we go.

Online dating continues to grow and some have begun offering their coaching and consulting services to help you navigate your way to the online love of your dreams. While I’m not a dating coach, I’m a small business and entrepreneurial coach, I can say I have a ton of experience in that world. (As a gay man who grew up in rural Kentucky, one learns to online date out of necessity more than anything. I’ve been at it since the dial-up days.)

So why not take some cues from both worlds and see how we can make them work in the other? Get ready for 7 tips that work in your business, taken from online dating!

#1 First impressions are crucial.
Make sure your first photo is a really great one. Flash a smile, have on a cute outfit, really reel them in with some intrigue. You don’t need to have a professional head-shot ready to roll (in fact that’s kind of a turn-off) but do put your best foot forward in the primary profile pic! You only get one chance for a first impression and you want to lead with your strengths.

#2 Be sure you’re well represented.
We want to get an idea of who you are as a person (or a business) and we can’t do that if you’ve just got one pictures or a single quick blurb about what you do. What are you hiding? You’ve got a camera on your phone and a keyboard on your computer. Show us what you’re all about! My rule for online dating is you should have at least 6 photos up because that gives us a real look at who you are. You’re a multifaceted person (and your business is too): show us all those lovely facets!

#3 Show us the real you.
We’ve all heard the horror stories of showing up for a date and the person looks nothing like the picture (or hiring an employee who looks nothing like their resume). If the only representation you have on your profile is your glamour shots then we don’t get a picture of who you are in the day-to-day. (I’ve always called these “best-light” photos. “The lighting must be amazing in his apartment” is code for “He looks nothing like his pictures”.) Show yourself caught in the middle of a laugh. Do you have any pictures of you making a face at your friends? How about one with you covered in puppies? We want to know what you look like when you’re not posing and primped. “Perfection” whether in a profile or in a professional pitch is a turn-off. There’s no such thing as a flawless business or person and your mistakes and struggles make you more relatable. You’re a human, so you’ve got some quirks. Let us see them!

#4 Intrigue, not explanation
Keep your profile short. We stop reading when it’s too long and besides, then there’s nothing to talk about on the date. “So I see you like Gilmore Girls, consider yourself a foodie, are best friends with your pug, don’t like seafood, grew up in the South, had a 4.0 in high school, prefer oreos over twix…” Pique our interest and make us reach out to you. Good online dating profiles are just like good copy, get to the point, make us need to hear more, then get out of the way.

#5 Don’t try too hard
There’s a fine line here between being prepared while showing you actually give a shit and coming off as desperate. If you wrap up your first client meeting with a hard push to hire or a high pressure sales technique then you’re less likely to actually gain that business. We’re in this for the long run so don’t come off as desperate. We can smell that on someone a mile away and even if we’re really interested, it can taint the most engaging exchange with an air of suspicion.  You can always let your potential suitor know you’re more interested in a long term thing without necessarily planning out your wedding, naming your kids, and picking out the window treatments (I was thinking wooden slats for a rustic feel but I’m open to a solid color curtain if it’s right for the room.) 

#6 Bless and Release
I am not a religious man but I stumbled across the expression “bless and release” and I have adopted it as one of my personal mottos. When you find that it’s not a good fit (client or date) it’s totally ok to bless and release them. There’s nothing wrong with you. There’s nothing wrong with them. This is just not a good fit. If you’re into meditation a nice little “may you be well” as you click that red X button feels pretty great.  If you’re running a business with an opinion or perspective (which I certainly hope you are…if not, maybe time to figure that out) you’re going to turn some people off. Same thing in your online profile. “Must love dogs” isn’t a good or a bad requirement but if that’s important to you, then someone who couldn’t imagine living with Mr. Wiggles is probably not a long term fit. You are not a fit for everyone and if you try to be, you will be a fit for no one. 

#7 Don’t take it personally
In business, as in life, sometimes it’s just not the right time. Sometimes it has nothing to do with you. Sometimes people just aren’t emotionally available. You are still awesome. Keep being awesome and don’t let one date not texting you back or one client not signing up mean anything about you and your worth.

So there’s 7 tips you can take into your professional and your personal searchings. Running a successful business can be very similar to having a successful relationship. Key components (communication, vulnerability, drive, commitment, compassion, and discernment to name a few) are valuable across the board. Whether you learn to cultivate those qualities on Match.com, OkCupid, Scruff, GlutenFree Singles, or at an investor’s meeting you’ll be more likely to “get lucky” with your ideal partner the more you can exemplify these qualities.

Now go out there and meet some people! If only there was a low pressure networking group with a monthly event somewhere in your area….

Strother Gaines
DC Director

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