I have a theory that relationship experts and coaches would decrease significantly in number if people spent more time dating and less time seeking a love connection.

When I first became single, I dated, A LOT.  I have no problem admitting that I fell into the serial dater category.  After years in a relationship that began as a teenager and ended with two children and dissolution (but thankfully, not disillusion), I had no problem embracing the idea of dating.  Life moves on, or it doesn’t, depending on the path you choose to take.  I chose the path of leaping into the dating pool with no floaties.

People attempted to hide their obvious shock but asked questions that hinted at it like, “you’re already dating?”  To which I replied somewhat cleverly, “we moved on, he didn’t die” or “my relationship status may have just changed on FB but my life changed some time ago”.  I was ready and it’s okay if that’s where you are too.  The easiest way to begin is by remembering that dating involves very little commitment–or at least it doesn’t have to and that you have the privilege of dating like an adult–as you wish and without apology.

When I began my mature foray into the world dating, I picked my way through options and opportunities, passed on some people and accepted invites from others.  I recognized that I wasn’t perfect and therefore wasn’t seeking perfection because it would narrow my pool drastically—and have me praying to the holy virgin fairy godmother for someone who didn’t exist.   I wasn’t optimistically ready for a relationship nor was I pessimistic about what I would find–I was willing to let things flow, so I put away the premier “dating advice” of my conservative Christian upbringing: Date to mate or Don’t Date Anyone that you wouldn’t marry.  While I can see the justification for that logic, I can also see why it is flawed when applied across the board, for three reasons:  One- You can’t determine if most people are marriage material without date level interaction (yes there are some baseline exceptions: marital status, employment status, etc), Two- Dating should begin as fun and unrestrained, not a gauntlet of tests and assessments, and Three- Some people are not interested in marriage, should dating therefore, be off limits to them?

 So, rather than focus on dating as a strategic, vetting process for marriage, I decided to make rules that applied to me and not the other person for the simple purpose of dating for pleasure.  This allowed me to build a fluid, dynamic but most of all existing dating life.  Here is where I started:


1) Be willing.  There will always be a reason to decline a night out.  If you find this to be consistently true of your behavior, you’re probably just not ready–and that’s okay.  Otherwise, be open, be flexible, and accept an invite or two, if there’s one thing that’s true about the dating world—it’s “no (safe) risk, no reward”.

2) Quantity does not equal quality but it doesn’t negate it either.  The point of dating is to have fun while you explore your likes and dislikes.  If you are one of the few people who meet’s their “soul mate” on the first date, good for you, otherwise, successful dating requires testing the waters.

3) Be open.  We all have our checklists but sometimes the unexpected can offer great rewards.  Put on a pair of flats for the day and go out with the guy that’s a few inches shorter than what you “typically like”.  In other words, change your dating pool totally. I circulated in a world of corporate executives limiting my exposure to (and interest in) blue collar gentleman.  After a happy hour date with a self employed mechanic, which included a mixed bag of conversation from successful business and marketing strategies to a heated but friendly conversation about our rival sports teams, I adjusted my perspective and discovered an entirely new type of “candidate”.

4) Use your time wisely.  One date doesn’t have to absorb your entire day.  I call this “brunch and bar” or “break fast for dinner” dates.  Simply put:  A date during the day, a relaxing afternoon alone, followed by a separate outing that evening.  I know this comes across as unconventional and may be uncomfortable, nor do I recommend it every Saturday, but it definitely keeps you from forming attachments and making commitments too soon during the exploratory phase.  The basic method to this reasonable madness, is to be as respectful of the other person’s time as you would want them to be of yours.   Don’t shortchange your date (or yourself) by reducing the amount of time you would spend getting to know them, go into the first outing with an open and clear mind (this wouldn’t be the time to plan your outfit for the evening), and don’t be crass enough to mention that you have a date that night–who knows, he may as well!

5) Converse don’t interrogate.  Rapid fire questions can cause anyone to feel tense and defensive—two words you don’t want to associate with any date scenario.  Easy conversation allows the other person to talk a bit about themselves and you to slip in a question or two, demonstrating interest.  If your company feels as though they’re being interrogated, it will likely work against you and create the effect of getting less information than you intended to.

6) Don’t feel a sense of obligation….TO ANYTHING.  This includes a second date, going home afterward, sex, or any situation that you’re not comfortable with.  The discomfort of declining an invitation is often what makes us hesitant to get into the dating scene.  Being willing and confidently saying “no, thank you” don’t have to be mutually exclusive!

7) Use a referral system.  I think that we often do ourselves a disservice by not introducing mutual acquaintances to one another or by not being bold enough to ask a friend “about a friend”.  In the sales world some of the best business comes from networking and referrals, the same bodes true in the dating world.  When people speak about the lack of eligible men, I often wonder about their friend and family pool.  Your aunt has friends who have children your age, your best girlfriend has brothers (or sisters) that have an extended friend list, what’s the harm in respectfully mingling or mentioning that you’re entering the world of the eligible?

8) Remain in a comfortable environment for both of you.  Unless you and your date are natural thrill seekers, keep the first time adrenaline rush to a minimum. Wouldn’t it be nice to know if he’s perspiring because he’s socially awkward or because you’re about to zip line between mountain tops?  Dating scenarios can be tough enough without adding uncontrolled elements like wall climbing, etc.  If you know your city well enough, suggest a favorite dining spot for drinks and small bites or something cultural, engaging, but unimposing like your local museum.

9) Leave the last date behind, in word and deed.  Your last date has no bearing on what your next date will be like so leave any bad experiences in the past.  Don’t reflect on them mentally and don’t mention them verbally.  The same could be said of good experiences.  There are no set parameters on “a good time”, the definition of an enjoyable evening can change based on the company you keep so don’t compare!

10) Be real.  The dating phase is all about discovery it isn’t about forcing a fit.  If someone doesn’t work out it, it’s okay to move forward on a high note at the end of the night.  As bold and outspoken as you may be, fearlessness doesn’t have to be hurtful, so leave the “you’re just not for me” conversations alone and politely decline IF you receive a call for a second invitation.  If the second invitation comes that night, you clearly may not be on the same page, so it’s best to say “call me and we’ll discuss it”–it’s not the cowards way out but declining over the phone can be a little more comfortable for both parties involved.

11) Don’t let the culture of shame influence you.  I believe that we have stopped dating for many reasons, including: that we move to the relationship phase with the ironic result of relationships that fail because we skipped to commitment too quickly or the perception of dating is that it must include physical intimacy.  Maturity means that we can build connections without passing go and skipping directly to the bedroom or that if physical intimacy is important, it happens without the burden of societal shame or judgment.  Build your dating experiences on the foundation of what is healthy and wise FOR YOU, if you’re not prepared to do that, you’re just not ready to date like an adult.

12) Don’t let your friends influence your decisions.  Your friends know your dating habits and type, and also have built a mental “like to have” list on your behalf, when you start to do something that is out of the ordinary–but may be good for you–don’t be surprised when you are met with resistance and doubt from the people who are well meaning but typically more cautious for you than they are themselves.  Take a chance and don’t be afraid to say, I tried and that one didn’t work, then do it all over again!

Ultimately, dating is a process that can end in a variety of ways, the only outcome that you should be seeking 100% of the time is safe, otherwise have fun and leave your preconceived notions home!