Real stories about dating and relationships in New York City. Truth is more interesting than fiction.

How Do You Spell Success?

I’m a very goal-oriented person.  Obsessively so.  That’s one of the reasons I like so much. I know, without a shadow of a doubt, that my efforts will yield results.  So, if I were to be really nerdy and look at this like an equation, it might be: minimal time + minimal money spent = dates with multiple men that I find interesting for one reason or another = goal achieved = success.   is a WIN for me.  I get that other people don’t see it that way, but whatever.

What about the dates themselves?  All of these dates (they do add up over the course of a year/years), are they wins?  Are they successful dates?  What is a successful date? Furthermore, what is a successful relationship?

Well, I started to think about that last week.  About the fact that I do, indeed, go out on a lot of dates.  And I’ve had more relationships (some short, some long) than the average person. The casual observer might assume that I am failing at dating and relationships – if that casual observer’s definition of dating/relationship success is wedded bliss or long-term monogamy.

Never happy with my own perception, I decided to reach out and ask the opinion of some people I respect. Here’s some of what they had to say:

Andrea Syrtash, dating/relationship , life coach and  author (most recently of He’s Just Not Your Type) – “Clearly if you’re interested in the other person and you book a follow up date, you will feel that your date was a success.  I think a really successful date is one in which you learn not only about a new person, but you learn a little more about yourself. That’s the best kind of connection you can have in a relationship — and the best kind of date.”


Tom Miller, aka Tomfoolery – “A successful date is one which the fun outweighs the awkwardness, effort and expense of making the date happen. Anytime that you had too little of each other to the point that you both have a need (or strong desire) to see each other again, socially and soon, you’ve had a nice date.”


The fabulous author of The Big Girl Blog – “I’ve dated a LOT in the city, but I’ve only had two dates where I as I rode the elevator up to my apartment (alone) I realized I was smiling. To me those were successful.

Someone once told me that we should end our relationships with as much delicacy and care as we begin them. I feel like if we follow that theory, all of our relationships can be successful whether they end in marriage or not.”


KB in NYC – “For me, the definition of successful dating would ultimately entail me meeting a man that I choose to have a meaningful long term relationship with. But I’m getting way ahead of myself because there are a whole load of ‘pit stops’ along the way. At one time a successful date for me was having a great night out with a man that I was sexually attracted to. It would usually involve a cocktail or two and a night of passion. Success! Now, making it to a second or third date is considered a success in my book. And acting ‘normal’ (whatever that may mean?) and not hopping straight into bed with a date. These things are all on my current barometer for a so-called successful date. I guess it’s about where you are at. And figuring out where you want to get to. One – sometimes fun, often frustrating – step at a time.”


Matt Brand, from Love in the Dumps – “Money spent on datetime spent on date is < (less than) or > (greater than) date experience.

Let’s look at some examples. If you spend $20 (two drinks) and one hour on a date experience that was mediocre (no chemistry and will not see them again, but the conversation was pretty good and you relatively enjoyed the hour you spent with them), the date was successful because the $ + time investment was not substantial. But bump those numbers up to say $50 and 2.5 hours with the same experience, and the date is a failure.

This gets tricky with women, who generally don’t pay for dates, or at most will spend $20. So let’s look at an equation in which they spend $0 but 2.5 hours on a bad date (no chemistry, you wont’ see them again, did not learn anything from the conversation and was not stimulated). They have to really think about those 2.5 hours. What could they have accomplished in that time? If they would just have watched reality TV or ruminated on their lousy love life in that time, the date was either successful or they come out even. But if they would have been productive in some way, or gone out to eat with an old friend, or called their grandmother, the date is a failure. So in this case (ie. Without the money involvement) it’s quite subjective.

But as a whole, I think that formula holds true.”


And last but definitely not least, Jack from Brooklyn – “A successful (first) date is one where you get to see if you really connect with someone. It’s a date where you can converse, see if you have chemistry, and decide if you want to see this person again. In my mind, this means that even if you figure out that you can’t stand the person, the date was a success because at least now you know where you stand.

A successful relationship is one where your needs/wants are met, and you meet the needs/wants of your partner. You feel safe, honored, encouraged, respected; there’s healthy communication and great sex. This may or may not lead to marriage, as people’s needs change over time, as does our ability/desire to fulfill them.

Success in my mind is defined by achieving whatever your objective is. From a relationship standpoint, you might want security. You might want companionship. You might want to get laid. You might want to be happy. Which makes the whole thing funny, because you might get any combination of the above, and still not be successful, relevant to your original agenda. You can also get what you want, but at unreasonable cost to yourself; pyrrhic victories don’t count as success.”

These are all smart and thoughtful people. All of them. And while there’s certainly some overlap to their answers, there’s plenty of disagreement. I find that oddly comforting.

In case anyone cares, I have no idea how to define a successful date.  Or a successful relationship, for that matter.  I know it has something to do with being happy.  With constantly striving to be happy.  And with pushing myself, taking chances, and going after what I want.  Fuzzy, I know. But then, I think dating and relationships are fuzzy topics.  My good date with Mr. Midwest the other night felt different than every other good date I’ve had in my life.  It was unique. As all people are different and unique.

I also know that, as much as I enjoy being in good relationships/having reliable partners in my life, I don’t view a long-term relationship as THE GOAL for dating. And certainly not marriage. That doesn’t even enter into my thinking (except here, in the blogosphere where I feel it’s an implied question, almost always).


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3 to “How Do You Spell Success?”

  1. Ken says:

    I’m at the point where a successful date is one in which nobody dies. That’s my new barometer.

  2. pups4me says:

    I think a lot about online dating and like you SG, I tend to overanalyze. I’ve been doing this for over 5 years and in that time I’ve been on lots and lots of first “meets”. Many of them were a waste of my time because there wasn’t even a glimmer of chemistry. Not only did I waste an hour or so of time on that first meet, I also consider all the time spent emailing and answering questions and getting up to the point when you finally meet face to face an investment in time. So when I add up all the time spent dealing with online dating, I don’t think I consider it an overall success, for me. Here’s where my analyzation comes in–out of all my first meets, I look at what % make it to a true first date. Out of these first dates, how many make it to a second, and then to a third. This is where the statistics are not in my favor and why I say I don’t think online dating is a success for me, with success defined as finding a long term relationship.
    There are good things about the online dating experience, and I would never say it sucks. I met people I never would have met in my day to day routine, and whether the person was someone I wanted to see again or not, it was an interesting experience.

  3. These are my equations (though basically you could say I’m on par with Ken)

    Conquering Nerves + Getting Dating Experience + Chemistry = Success

    Conquering Nerves + Getting Dating Experience + [NO Chemistry(Hilarious Blog Material)] = Success