4 Dating Realizations I've Had at Age 29

Over the past decade, my strategies and perspective on dating have evolved, and I feel better about the process. I'm less stressed about it because I have more realistic expectations: Most of my dates are mediocre, but that no longer distresses me.

I admit that my new strategies have not been more successful -- if we define success as securing a partner with whom I intend to spend the rest of my life and raise children. However, if we define successful as believing, "yeah, that could happen if I carry on this way" as I thrive and progress in other realms of life, then yes, my current dating strategies are successful.

So, if you want to be as successful as me at dating (meaning I'm quite single, but cool about it), here are some tips:

1. Invest minimal time, energy and emotion on the first date.

When I first began online dating, I set up exhausting, time-consuming dates. Dinners on Saturday nights on the other side of town. I would fuss with my hair and makeup, try on multiple outfits -- taking time to "look hot."


Sequin mini-skirt... this will snag me a husband!

During the bus, T or taxi ride across town, I would envision our potential love story. I have an active imagination fed on rom coms and nuclear family norms, so my pre-date fantasies were a bit domestically aggressive. What would it be like to date and marry and have kids together? I'd wonder before I even met the poor guy.

And then he would be a surprisingly short, Boston a**hole type, who was more on the unemployed side of the freelance-unemployed spectrum than I would have liked.

Him: "Yeah, McFadden's was the best club in Boston. Now it's closed, so probably Ned Devine's is the best club in Boston. I'm looking into doing some marketing there."

By marketing, he meant having hot chicks pass out free hats with his "brand" on them.

Goodbye, Saturday night that I could have spent gabbing with friends over cocktails or consuming Daily Show episodes and chips and salsa at home! I begrudged him for ruining both my Saturday and my plan to fall in love with him and wed within the next 3-5 years.


He dashed my hopes of this in 3-5 years...


...and this on that particular Saturday night.

Effortful dates were a bad strategy for me. The predate prep and buildup led to unrealistic expectations, so invariably, I was disappointed. It was just bad economics: high investment, low return.

Now I arrange dates two blocks from my apartment at a bar that is practically an extension of my living room. We have one to two beers on a Monday. I wear whatever I was already wearing that day and my pre-date prep consists of checking if there's anything in my teeth. If the date is mediocre, whatever, I had one to two beers at my favorite bar on a Monday, which is probably what I would have done anyway. If the date goes well, next time, we can get dinner and I'll wear lipstick.

2. Exist as many places as you can (without going too far out of your way).

You're not going to meet anyone alone in your apartment without the Internet. It sounds patronizingly obvious, but you need to be places -- both real and virtual -- where you will meet new people.

So, when your department is having a happy hour with another department from the third floor, just go. When your friend from college invites you to a party and you won't know anyone but her and her husband, just go. Use online dating and app dating. When you have work to do on a Sunday afternoon, do it at a coffee shop rather than at your kitchen table.

You probably won't meet someone at that coffee shop -- I've worked at coffee shops at least 12,000 times in the past five years and never once got a date from it -- but you definitely won't meet a date alone in your apartment without the Internet.


I have a lovely home office, but I'm not going to meet anyone there (except my lemur stuffed animal).

3. Be selective.

When I started online dating, I aimed to sample the diversity of men. I went out with lawyers, teachers, chefs, engineers, freelance web designers, horse whisperers and the unemployed. I tried tall guys, short guys, overly fit guys, nerdy guys, older guys, younger guys, sub-attractive guys and men of different nationalities. I thought maybe I didn't know what's good for me, so I was willing to go out with anyone non-murdery-looking.

That was a mistake. There are some qualities that I require, at least at this point in my life. I need someone intellectual and accomplished with a sense of humor, whom I am attracted to and who live within a five-mile radius/can agree to meet at that bar two blocks from my apartment on a Monday for one to two drinks.

Tinder is a great tool for improving your selectivity. I used to deliberate before a left swipe -- really assess the pictures from all angles, squint a bit. Now I'm assertive and swipe right for about 1/20 of the profiles. 5% approval rating may sound depressing, but it is realistic and efficient. Better than meeting all of those people in person!

I involuntarily and audibly react to ones that are preposterous to me.

Muscular dude in a tank with a prominent tattoo on his bicep. "BAH!" Left.

Lineup of three guys with dipshit grins standing next to shiny girls in a club. "GAH!" Left.

Sad guy sharing a pillow with his cat. "ACK!" Left.

No picture. "Pfft." Left.

Digitally drawn self-portrait cartoons. "Ughhh." Left.

Is that a passport photo or are you just that angry? "Eeee." Left.

Handsome, tussled hair, but clean-shaven engineer who "likes beer" within one mile. "OH!" Right.

4. Realize that it's about the connection between you both and not your quality as individuals.

I've come away from dates enthusiastic and swooning, thinking I came off as indisputably charming and certain that a fulfilling relationship would ensue. And then he never wanted to see me again. Either he disappeared or claimed that he would be busy for the foreseeable future or our text-exchange just dwindled into nothing.

I would force my friends to analyze insipid texts. Where did I go wrong? What did he mean?

Me: "It was great meeting you! Let's do it again soon."

Him: "Yeah, definitely!"


Me: "How's it going?"


Him: "Fine! How are you?"

Me: "Great -- how about drinks Thursday?"


Him: "Sure! I'll text you tomorrow."


Him: "Hey so sorry to do this but a lot of stuff came up at work so I can't make it. Maybe sometime next week?"


Okay, I get it. He's not interested. BUT WHY!? My acceptance of his non-interest is paired with indignation. Doesn't he realize how good we would be together? We have so much in common. We're both from Pittsburgh and living in Boston. He went to Brown and I went to Dartmouth! We both like spicy food and dogs! My hair looked great and I was witty and impressive and asked him the appropriate number of questions! How could he not want to date me?

But I've also been on the other side of that situation. I have gone out with kind, attractive, accomplished individuals who fulfilled all of my aforementioned criteria. I really wanted to like them, but I didn't. I felt, "meh," for no determinable reason. I could have gone out with them six dates more, two months more,or never again, and it wouldn't have made much difference to me. They were good men. I am a good woman. We just didn't have the right connection.

This realization is what calms me to the whole dating process. It's not you; it's not them; it's you plural and finding a good you plural is tough, especially when your starting pool is only 5% of the Tinder population.

Other components of my life are great -- work is fulfilling, my friendships are fun and supportive and my favorite Spinning teacher Kara is teaching on Thursday nights. I'd rather go to Spinning with Kara, followed by beers with friends (to immediately retox) than dash across town for a blind date. Mondays are date nights because that's what's convenient for me right now, at this stage in my life. I'm not scheduling my life around dating -- nor am I letting the outcome of particular dates overly weigh on my emotions or hopefulness. But I am selectively dating and "putting myself out there" and this is a good strategy for now.


I have yet to find a life-long mate, but I have sampled many wonderful beers!