Saturday, November 29, 2014

Ten Things I Learned This Year About Dating


The month of November is drawing to a close, and for me that means it’s time to start looking at New Year’s resolutions.  New Year’s resolutions are probably my favorite thing about the holidays, because I’m extremely goal-oriented, love lists, and am constantly looking for ways to self-improve.  It’s also a time to dust off last year’s list and see what I did well and what clearly needs to make it another year on the list.

This year, one of my big goals was to date more.  I didn’t necessarily put “date successfully” (because then it would have been a giant N-O on whether I passed it), but just to go on more dates.  As a result of this, I have been on roughly 30-40 first dates in the past year.  That may sound like a lot, because it is-I joined both Match.com and OKCupid and wanted to make a go of it, because I hate when people A) only half-heartedly pursue what they want and B) I was sick to death of people saying I was still single because I wasn’t trying hard enough.  So this year-forty dates in, that statement cannot remotely be said anymore.

Overall, the success rate was pretty lousy.  Part of going on this many dates is that you’re going to run into a lot of guys that are not good matches-the reality is that the awesome guys are harder to find principally because they’re probably already taken.  I’m not old, but I’m not young anymore.  In the past year, I had one boyfriend, several really good dates, a number of second dates, and a healthy number of “please-never-call-me-again” texts that I had to send.  As a result, I’ve learned ten key lessons about dating that I’m going to share with you now, and hopefully you can either use them in your own dating adventures or use this advice for your single friends when they come to you wondering why he/she hasn't come along yet.

Just cause he's cute, don't invent a personality around him...
1. Dating Profile ≠ In Person

This is easily the biggest lesson for me, since I have not dated this heavily in a while.  Thanks to texting, snapchat, instant messaging, 10,000 OKCupid questions, and of course a good old-fashioned Google search, you can know almost everything there is to know about a person before you actually meet.  You don’t have to worry about questions about if they want kids, whether they like dogs, are they into the same music, etc, etc, etc.  That’s all on the internet, in neatly categorized boxes.  It’s like trying to make Barney Stinson’s Lemon Law (from How I Met Your Mother, it’s a theoretical rule where you can stop a date within the first five minutes because you know it won’t work out) completely obsolete.

Except, of course, that it doesn’t do this.  People, for some reason, never seem to quite match their profile.  It's partially because we know about 70% about them, so we magically try to fill in the remaining 30%.  And this is particularly bad, because that 30% is probably where the chemistry is going to lie.  I could meet someone who loves the same movies as me and I find attractive, and seems very cute in texts, and when I meet him in person, the slight asides he made complaining via text about his life come across as grating and whiny in real life, the Bohemian aspects of him working a night shift at a bagel shop while pursuing his art make way for him being completely without ambition, rather than him just being Keith Carradine in Nashville, and that novel that he’s working on and is oh so proud of-yeah, he hasn’t written anything in four years, but still fashions himself a writer with some faded college term papers being the last thing he actually wrote.

I always feel like putting some advice into the world, so just try not to lie in the profile.  Your personality can't completely come across, admittedly, but don't purposefully deceive.  If you only passingly like camping, just skip it.  We all want to date a guy that looks like the Brawny paper towel man, but we’re not going to get him by pretending to like the outdoors-he’s going to catch on pretty quickly that we'd rather be inside eating Ben & Jerry's while watching Orange is the New Black.

2. Maturity Levels Become More Pronounced As You Get Older

When you’re 23, you really don’t notice maturity levels, because, no matter how old you think you are, you aren’t really that old.  You spend your days almost exclusively around people your own age, you still have a “don’t tell me what to do” relationship with your parents, and you are still figuring out where your career path will lead you.  In your late twenties/early thirties, though, all of these things are eventually sidelined.  Your backup plan doesn’t become living with your parents, but instead relying on your emergency fund.  You can have a Saturday night where you don’t go out, but instead stay in and don’t feel lame for doing it.  And things like a 401K, health insurance, mortgage payments, and an Excel spreadsheet with your expenses become something that you just do, rather than remain befuddled and have arbitrary stances against primarily because you don't actually understand them.

Except it doesn’t happen at the same speed for everyone, and this becomes extremely awkward.  You find at this point that there are still people who haven’t started saving for their retirement, haven’t gotten to the point where getting completely wasted is a couple-times-a-year thing and not a weekly thing, and where they spend money without any regard for what will happen next in their monthly budgets.

This is made more defined by the fact that most of the people you spend your time with at this point are, in fact, similar to you and have a similar set of life goals.  If you are spending every Saturday night smoking pot and playing Settlers of Catan, or if you’re spending Saturday night at the movies with friends, or if you’re spending Saturday night staying up until 4 AM macking on the hottest person that would have you at last call, chances are that most of your friends and coworkers are doing something similar.  This is a problem in some ways because you know that everyone else in your world is one way, and you know this person won’t fit in as a result.  One of the best pieces of advice I’ve received on dating in your late twenties and beyond is that you notice and are aware of things that you would have overlooked or not noticed in your early twenties.  As a result, you tend to get pickier more as you learn more about yourself.

It’s also hard with this particular issue not to treat it with a solid amount of snobbery.  You have people who go partying who think that someone is “boring” because they spend Saturday nights in rather than going out.  You have people who think someone living at home is a sign that they don’t have ambitions, when really they are just trying to save some cash.  The problem with this is that it isn’t snobbery, exactly, but it’s just different attitudes and life paces.  However, it is important, which is why you should be aware of it.

3. Judging a Book by Its Cover is Essential

Here’s the deal.  It’s wrong to not date someone just because they look a little bit chubby in their profile pictures or they might not have as much hair as you were expecting.  That being said, in a sea of hundreds of profiles, you need to find some way to distinguish, and judging a book by its cover is critical in determining who gets an email or a response, and perhaps even a date.

Since I was initially less discerning, I learned some shorthand while reading through a profile:

-People who only put one picture generally don’t look like that photo
-People who have no hobbies other than “hang out with friends” listed are generally pretty boring and you're going to have to carry 90% of the conversation
-You can tell in the employment section whether or not this person is content with their career
-If they complain more than twice in their profile, that’s all they’re going to do during your date
-If they are clearly drunk/high in the photo, you should expect that in person
-People who don’t have at least one clichéd favorite book probably aren’t regular readers (clichéd books include Harry Potter, The Hunger Games, and anything by Dan Brown or John Grisham)
-People chose photos specifically of things they like to do-if they are traveling in all of those pictures, expect someone who travels.  If they are sitting in a room in the dark wearing the same black tee in all of those pictures, that’s also what they generally do.
-People who are over 28 and use phrases like "I don't really feel like an adult yet," are saying that as a catch-all excuse for when you're stunned that they don't have a retirement account or that they get drunk on Wednesdays.

The reality is that what people put on their profile is how they want you to perceive them.  It may not eventually reflect who they actually are, but I’m going to be honest here-it rarely gets any better than that, so if the profile isn’t interesting or compelling, they probably won’t be either.

Cute, nice, and completely boring is a poor combo
4. Nice Guys Finish Last…If They’re Boring

Nice guys are awesome, and it’s really all you’re looking for in a dating profile-someone nice, smart, and responsible to spend your days with, and the cliché that “nice guys finish last” is pretty worn and not at all true.  A truly nice, considerate guy is going to be snapped up pretty damn fast on a dating website.

That being said, nice guys of the world-you need to make sure that your personality shines through on a first date.  If you just go in and are considerate and offer to pay the check, that’s sweet, but it’s not going to discern you from the pack.  You need to show what you’re passionate about, even if the other person isn’t.  I remember one of the best dates I had all year was with a guy who was really interested in hockey.  I don’t know a damn thing about hockey, but he had a passion for it, and that spoke to me that he was someone that could take a vested, long-term interest in something he didn’t have to (we all have friends, family, and jobs-what you do with your free time is how most people will judge you as the rest are like the free space in BINGO).

And if you aren’t passionate about anything other than work and friends, maybe it’s time to start.  Travel, sports, the arts, volunteering-the list is limitless, but it’s time to find your personality outside of what society is mandating of you, because it shows that you’re someone who wants to a grow as a person, and that’s always attractive.

5. People Skills Are Critical

I will never quite get over the date I went on this past year where he never asked me a single question over the course of an hour.  It was mind-numbingly bad.  The problem was that he wouldn't have been that awful if he had engaged me at all.  He looked a bit older than his pictures, but we did have a couple of similar interests.  However, the fact that he was clearly not interested in my personality at all, or getting to know me, was a big turn-off.  And I always end this by saying he texted me several times afterward wanting a second date, so clearly this wasn't a ploy to get me to end the date quickly-he was still interested, but completely shot his chances to hell by seeming so egotistical.

This is why it's so critical to keep your people skills sharp.  Look at it this way: on a first date, if you haven't asked them a question in five minutes, you need to turn the conversation back to them.  We occasionally see dates on TV where one character ends up talking about their life story for twenty minutes, and says "well, enough about me," but in real life you need more give-and-take.  In some ways, the old Carrie Bradshaw adage "first dates are like job interviews with cocktails" is pretty much dead-on.  You want them to leave impressed by you, but also that you were interested in them.  That's not hard-you do it all the time in real life.  If you're someone who is shy around people they first meet, then just ask them a lot of questions-it will show you were interested, and people love talking about themselves.  When it comes to answering about yourself, just be truthful, or talk about what they were interested in-it's pretty simple, and will give you a leg up because if the past year has taught me anything, it's that texting/IM-ing/snapping have made it much more difficult for my generation to hold down a proper conversation.

6. OK First Date ≠ Good Second Date

I was once given advice, very early on in my dating life from a married friend who said she didn't like her husband on their first date.  She thought he was kind of standoff-ish and didn't think the second date would go anywhere.  However, she had a policy that unless the first date was a disaster, she gave the guy a second chance in case he was shy on the first date.  In this specific case, this ended up being the best romantic decision she ever made, as they ended up happily married and with a baby girl.

However, this is the extreme exception, and not the rule.  By-and-large, most people who get the OK first dates generally just end up being a growing snowball of OK as you continue.  The problem with the OK dates is that they gain that status because you didn't really have an opinion on them.  Great first dates are the ones where you don't really want them to end, where you're giggling at the car afterwards hoping that someone will ask for a phone number or to see each other again or even if there will be a good night kiss.  Great first dates you know because you're hoping for a text message the next day at work, randomly looking like a rabbit at your desk every time you see the phone screen light up, and either jump for joy when you get a "how's your day going?" or get royally bummed when it ends up being a Pinterest alert.

Conversely bad dates you can tell because you know you never want to see them again.  They were giant jackasses or egotistical jerks or spent the entire date complaining/whining/mumbling.  Like a great date, you can tell what was wrong with a bad date.

OK dates are hard because you can't put a finger quite on why they didn't click.  I had a date like this recently.  Nice guy, smart, had a decent job, and was relatively engaging on the first date.  In my head I thought, "well, this is what you're looking for" but chemistry is something you can't force, and I wasn't into him in a dating way, he just happened to match what I was looking for.  These cases are weird because you're both good people, and I'm positive this particular guy will make someone very happy someday, but I could tell it wouldn't be me.  If I followed my friend's advice up-top, I would have gone out with him again, but I could tell that it wasn't nerves keeping him from being a great match, but just that he wasn't for me.  And in those cases, it's fine to end it after the OK first date without going through with the second, and not feeling guilty about it.  (Small caveat-if you are leaving every date with this feeling, you might need to figure out what you are looking for, or at least pursue a second date with a couple of guys as your first date skills may need to be sharpened).

7. Dating is Expensive

This is going to make me sound like Fred Mertz, but I don't care-dating is expensive.  Part of the reason that I push for coffee on a first date isn't just because I think it's a much more appropriate setting for conversation than dinner, but also because coffee costs $4.  You go on as many dates as I have in the past year, and you start becoming more discerning out of sheer economy.

This is partially a John-specific gripe, but it's something to keep in mind before you pitch dinner on a first date.  There is frequently an income disparity between two people as they get older, and so it might behoove you to suggest coffee or a drink on a first date if only because you won't feel guilty about taking someone out for a $17 meal...and you won't feel the need to have to pick up the check for what ended up being just an OK date.

8. Dating Advice is Stupid and Contradictory

Dating advice, and particularly when it's cliched, is so often silly and stupid.  The reality is that almost all cliches are contradictory when it comes to advice.  An example of this would include "you're being too picky" and "don't settle!"  Or "it will happen when you least expect it" and "you have to put yourself out there."  More than most topics, dating advice, perhaps because most people aren't good at giving it, generally tends to just push people in the opposite direction of where they are headed.

I want to, before I move on to Number 9, address specifically the "don't settle" thing, because for both married and single people I think this is perhaps the most abused and misunderstood cliche of dating.  The reality is that we all settle when we get married or decide to be in a relationship (or quite frankly, when we decide not to be).  Single people, pay attention-your married friends, if they're being honest with you, have something they can't stand about their spouse.  Maybe they smoke when they drink and they hate that, or they leave their socks on the living room floor, or they frequently start projects without finishing them.  The fact that they put up with this but don't leave: THIS is settling.  And it's not at all a bad thing-you'll never end up with someone who is perfect for you, because as human beings we'd find a way for even that to drive us crazy.

What people are frequently talking about with settling is ending up with someone because you don't want to be alone.  That's the settling that everyone protests, and rightfully so.  You shouldn't want to end up with someone who won't make you happy just so you don't have to check "single" on wedding invitations (no matter how much that might seem like a good idea when you're buying yet another set of bed sheets and sitting at the singles table, which looks more like an episode of iCarly than it does a group of peers at this point).  If you fall head-over-heels in love with someone, but they are not at all what you expected, and your friends are saying you're settling, as long as they make you happy-that's the point.

9. Unsuccessful Dating Can Be Oddly Rough on Your Friends

I think one of the biggest realizations that I had over the past year was how tough unsuccessful dating can be on your friends and family.  At a certain age (this age varies depending on what part of the country you live in, but every area has it) you come to a point where most of your friends/family are married.  In my case this is basically all of them-all of my close family, college friends, and pretty much all of my close coworkers are either married or on their way.  As a result of this, I'm frequently trying to pick up tips from the ones in successful marriages on how they met, ways that I could emulate how they met, and whether they have any single friends that might be a good match for me.

The "rough" part here isn't that you have a whiny single friend, which I think is what I always thought was the rough part of this equation, to the point where I personally wanted to stop talking about dating entirely with my friends so that I wasn't a Debbie Downer.  The rough part is that your friends want to help you, and in this specific but very major part of your life, frequently they find themselves without helpful suggestions.

Look at it this way-if your friend is having trouble at work, there are a number of different easy pieces of advice that you can give to someone to help them out: ask for more projects, learn more about promotion opportunities, see what additional education might help, try to emulate people who have better work-life balances in your office, etc, etc, etc.  The same is true for buying a house, losing weight, reading more, planning a vacation-there is no shortage of advice, and frequently good advice, that friends and family are willing to pitch in hopes of being helpful.

With dating, though, the biggest obstacle to giving dating advice is that there's a great deal of luck involved with romance.  The fact that someone met their future spouse at 19 and another person didn't-part of that is luck.  But admitting that something was just luck isn't good enough for either the single or the married friend, principally because the single friend can't create luck (despite what Billy Zane might proclaim) and the married friend can't replicate it.

The other part of this being rough is that being in a relationship for a long time starts to jeopardize how you can connect to your single friend in this sphere.  Unless you sit back objectively and think of how reliant you are on your spouse for emotional support, financial support, or just being someone whom you know will go with you to your cousin's wedding or to an office party, it becomes so commonplace that it's a bit jarring to try and step into your friend's shoes.  Realizing that you cannot connect with your friend in this way may result in you closing off conversation with them in this avenue by saying, "I just don't know how to help," but here's the thing-the problem still exists at that point, it's just now the single friend has one less person to bounce ideas off of.

Lastly, and most importantly, they're your friend-you want to help them.  Unless the friend has no interest in long-term relationships and is simply interested in short-term relationships, you know they're trying hard, and continued failure in this avenue is doing no favors to anyone's self-esteem.  I think that the "what can I do?" aspect of advice from friends was really a key understanding for me this year-it's hard to volunteer to help on something you don't have any ideas regarding.

So here is my advice to you if you have a friend that is continually single, and you're out of options: volunteer to be a wing man (or woman).  Honestly, this is probably the best advice I can give at this point for three reasons.  One, it might actually work.  Your friend is probably trying online dating, and may just need the confidence of a night-out of bar-hopping or going to a singles mixer or a night of OKCupid window-shopping with a glass of wine.  And you pushing them a little bit outside their comfort zone to talk to the cute guy at the bar or to send a message to the girl that just checked out their profile-that might help.  Secondly, there's a decent chance you have absolutely no idea what your friend's type is (I'll be honest here-most of my friends/family couldn't pick out my type in a lineup even if they think they could, and are basing their ideas of my type more on their impression of me than on any actual evidence), and this will give you a better understanding, and may make you rethink setting them up with that guy from your yoga class.  And third, it's trying something different.  Sometimes the placebo effect is a real thing, and having the sense that you have an ally in your seemingly fruitless quest for dating-that's a powerful boost to you to want to continue.

10. Reevaluate Dealbreakers

Finally, the last thing I really learned this year was that dealbreakers are real things, but they aren't exactly what you think of when you list out your dealbreakers.  Usually you think of dealbreakers as a movie that you love or them being Packers fans or that they're taller than you, but while these may be your dealbreakers, you'll break these pretty quickly.

What you won't break is the things that would genuinely make you uncomfortable.  I have been on dates with guys who I knew would not mesh well into my family, and while me at 22 would have said "my family can adjust" me at older-than-22 realizes that this is code for not meshing well with me, as on a first date you're going to pick your family over your date every single time.  I have learned, for example, that someone without any sense of ambition or purpose to their lives, coasting through without any sort of game plan, is not for me.  I have learned that conversation is way more important to me than I initially gave it credit for-someone who can challenge how I think, but also is willing to challenge themselves-that's for me.  And yes, I still like guys who are taller than me (I'm short-it's not a hard bar to cross).  But as you age and continue to learn more about yourself, your dealbreakers tend to reflect that.

Those are my ten key learnings from the past year of dating-what about you?  What are some things you've learned from your resolutions this year?  What are some of your key dating/romantic insights or learnings that you've picked up on?  Share your thoughts in the comments!

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