Passing through the Wharf by the waterfront, I recalled why I hated driving into downtown Boston in peak rush hour on a Friday evening.  I eventually navigated through the crowd and found myself at the Landing along with a few buddies.  We quickly immersed ourselves in a conversation about the difficulty of dating and meeting the “right” people.  The irony of the urban dating environment (according Marina Adshade – see REF) is that as the opportunity cost of meeting new people decreases, we automatically increase our selection criteria to adjust to the change in the dating market.

In all cases, I can’t solve your dating problems but I can offer a few good suggestions from folks who have studied this extensively (Adshade, Fischer).  To make it more relatable for you Boston readers, I’ll discuss this via some concrete date ideas as you progress through the different stages of your burgeoning relationship:

Date # 1: First Things First – Dorado Tacos

For most people, first dates can be nerve-wracking, especially if you’re seeing each other for the first time (online dating) or after a night of drunken debauchery.  The uncertainties will start to settle in with questions about whether the person will like your jokes or your smile.  With so much potential angst and risk, don’t invite her out for a large 5 course meal.  Instead, go for something casual like Dorado Tacos (Please note I don’t get any royalties for endorsing this place).  This place is excellent for that first real encounter because the conditions are perfect.  Location wise, the Dorado is situated on a quiet Brookline corner (near JFK’s birth place).  When weather is permitting, you can even be seated outside with your beer and tacos.  This is important because YOU want to be in a casual public environment for the first date (in case your date has bad breath and you need to run?).  And if things are going well, seeing all the newly minted parents parade around with their strollers will only further ignite her interest to initiate a serious relationship.  Lastly, this is one of the few places in Boston that serve alcohol and tacos NOT packed with hipsters and loud music so a good conversation can ensue.  Keep the conversation light and suggest a second date idea if all is going well.

Date # 2: Hips and Dips – Salsa at the Havana

If you’ve made it through the beers and the tacos without a hiccup, then you’re ready for date numero dos.  No checklist in the world will help you find someone with the right chemistry and the most effective way to find out is through physical encounters.  This can vary for a great many people but Friday night Salsa Lessons at the Havana Club is a fine starting point. Why?  Let’s just say that there aren’t too many social situations where a semi-stranger will let you hold her hand and her waist as both of you gyrate to latin jazz.  This is an important step because it helps to identify if there is physical chemistry early on in the process.  For those not rhythmically inclined, the Havana offers free group salsa lessons earlier in the night which allows you to ease into the dance.  Much like Salsa, dating is a game of giving and taking. If she’s not grooving to the same tune as you (emotionally and physically), then that should be a warning sign.  Pay attention to small physical cues like if you tighten her hand in your hand, does she reciprocate?  If you lean in or hold her waist slightly closer to you, does she resist or does it pique her interest?  Are you maintaining sustained eye contacts?  Chemistry is the secret sauce and if you can unravel the recipe, then you’re ready for the basics.

Date # 3: Back to Basics – Otto’s then Coolidge Corner Theater

Movies are generally bad first date ideas because it does not give you room to learn about one another. BUT if you’ve made it this far, going back to the basics can only amplify your connections.  Start the evening off at Otto’s Pizza near Coolidge Corner. It’s a quick and hip place to get some surprisingly good thin crust pie.  Next, head over to the Coolidge Corner Theater (across the street).  This place will send you back in time as one of the last art deco theaters in New England.  Pick a seat in the cozy theater, snuggle up with your date numero tres and a pint of your favourite brew (yes, alcohol IS allowed here).

This is a perfect 3rd date for a multitude of reasons.  Agreeing to a dinner and a movie is at least a 4-5 hour long commitment.  Anyone who agrees to spend 4+ hours with you on a weekend evening is likely to be interested in having a relationship with you.  You’ve already learned about her life at Dorado’s, you’ve learned about her physically at the Havana, now you’ll learn if she can handle being silent with you for an extended period of time.  This helps to establish if she’ll be comfortable just being next to you.  Lastly, because of the commitment, the movie scheduling, and selections, this date is your first opportunity to plan something together as a couple.  There is meaning in the silence and if you’ve made it this far, she’s ready to see your friends.

Date # 4: Seal of Approval – Grassfed Jamaica Pond

My dad once told me that you’re the average of the closest 9 people in your life.  So pick your friends wisely (that’s a post for another day), especially if you’re planning to spend the rest of your life with this person.  On your 4th date, take her and 2-3 of your closest friends to Grassfed for some locally sourced, grass-fed burger.  This hole in a wall is only minutes away from the Jamaica Pond which is a much more scenic place for dining and conversing.  Find yourself a nice bench or a patch of grass to sit on and enjoy the sunset over the pond.

New friends are great but old friends are better.  Having a casual date with your friends provides them an opportunity to learn more about her directly.  This is a double-edged sword because it allows them to provide a different perspective (that you may have missed as you are now gaga over her) and it allows you to evaluate her thoughts on your friends.  If she responds positively, she may likely set up a date with you and her closest friends 🙂

Date # 5: Ask the Right Questions – Pavement BU East

I added this last date suggestion as a bonus.  There was an interesting article from the New York Times examining if love can be synthesized by a series of increasingly intimate questions.  You can find the questions on this link here.  The game is very simple.  Take her out to Pavement (by Boston University), find a quiet area in the back corner and ask away.  This list of questions will help you identify the nooks and crannies of life that you’ve never even thought about such as big wedding or small wedding? when was the last time you’ve cried? Tell me what you like about me?  Yes, these are incredibly personal questions and most people refrain from asking or answering.  This is why the 5th date is what I’d consider the threshold date.  How much she’ll open up is an indication of her level of trust in you and her commitment to have this be a meaningful relationship.  This environment allows for an open disclosure of feelings, plans, personal worries and everything that aggregate to a meaningful connection.

Relationships can be fickle, particularly in our technology driven world.  It doesn’t have to be this way.  Learn to invest in the few relationships/things you ACTUALLY care about.  You’ll find that it’s rather liberating.

REF: Why Him? Why Her? – Helen Fisher

REF 2: Dollars and Sex – Marina Adshade


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