Date UpDate

Sometimes I feel like I blink and months have disappeared.  That’s how the remainder of the summer went for This Dater.  July, August, and now September, gone.  There were lots of dates and there was lots of life.  The highlights:

Unstable on Purpose Dude – more stable than originally appeared.  We’ve been on a handful of dates (handful = more than 5, less than 10) over the last few months and I guess you can say he’s still in the picture.  My filter-free conversation with him continues; subjects have ranged from family to past relationships to politics to sex to therapy to hopes for the future.  I’ve come to appreciate this mutual honesty – even when I asked him if he was in relationship mode or casual fling mode.  Unstable on Purpose Dude is in a unique spot where he has the ultimate freedom of not being tied down by a regular schedule, and he travels a lot.  Like every other week.  While he’s not opposed to a relationship, he is scared of feeling resentful towards the person that takes away this potentially short-term freedom.  So that was a fun conversation.  I am going to see where it goes with Unstable, but have noticed myself pulling back a bit.  Can I let myself fall for someone who might pick up and leave at a moment’s notice?  And then last week he goes and sends flowers to my apartment.  What?

The Most Interesting Man in the World – less interesting than originally appeared.  I was infatuated pretty quickly with TMIMITW.  He was foreign, spoke many languages, and was a true gentleman.  He also sent flowers – after our first date.  Again, what?  Where are all these flower-giving men coming from?  Our dates probably add up to a handful and a half over the last couple of months.  While I was originally in awe (and even a little “am I interesting enough for him?”), the more time we spent together the more it was evident that we didn’t have that much in common.  While TMIMITW knows how to woo a lady, I often didn’t feel like myself around him.  Turns out This Dater likes a wee bit of wooing, but I also need a healthy dose of silliness and sweatpants – things that weren’t likely to happen with Interesting.  TMIMITW is also gone a lot so things sort of naturally came to an end, I think with both of us realizing it wasn’t a match. 

The Guy Who Doesn’t Want to be Written About – the end. 

This Dater – admittedly has been in a funk and is just now coming out of it.  I approached this whole “I’m single and 35 and DATING!” thing with a positive attitude, but honestly sometimes it really sucks.  Everyone around you says appropriately encouraging things like “You’ll find the right one soon!” and “Lucky you, it must be so much fun!” but there are times when it’s not fun and This Dater wants to kick encouragers in the shin.  Not really… but kind of.  Going to a wedding where you are literally the only single person on the party bus sucks.  Third (or fifth, or seventh) wheeling to things with your coupled up friends sucks.  Having your parents – who have never before put pressure on you to settle down – say those same appropriately encouraging things sucks.  Seeing everyone around you have beautiful weddings and adorable babies and feeling excited for them but also like you are so far from it for yourself sucks.  Add in the fact that your usual coping skills for suckiness are no longer useful (i.e. getting wasted) and the thoughts of your ex that start to creep in (i.e. he wasn’t that bad) and the result is a super negative suck spiral that you didn’t even realize you were in.

This Dater was talking to her therapist recently and she gave it to me straight.  She gently reminded me that one of the things I struggle with is patience.  I was wanting to jump right to what I thought was the good part of a relationship; rolling over and seeing the person you love next to you in bed, knowing your Friday and Saturday nights won’t be spent alone, and wearing PJ pants while spending the day ordering takeout and reading together.  She said something encouraging, yet I didn’t want to kick her in the shin because it really made sense to me.  By wanting to fast forward to the “good parts,” I end up missing another category of “good parts.”  Getting to know someone new.  Getting to know myself better.  Flirting.  Butterflies and nerves.  First kisses.  FIRST KISSES!  Once I find my forever person, there won’t be any more first kisses.  I’m pretty sure I’ll eventually find my someone (yes, encouraging friends and family, I hear you), but why the heck am I rushing through all these other good parts? 

So summer is over and fall is here – it’s a new season for This Dater.  I’m rearranging my closet and rearranging my attitude.  Dusting off boots, layering up, and heading back out there looking for ALL the good parts.  I know there will probably be some more suck along the way, but that’s ok.  Slowing down and getting myself out of the funk is a lesson I didn’t expect to come out of this journey, but – dating or not – it’s probably a good life skill to have. 

Do I Need A Filter?

Dating apps are fun.  It’s like playing a game – granted, a horribly shallow game where you decide if you want to talk to someone based solely on their looks at first… but in the world of dating, these apps aren’t actually that far from how it works in real life: you are cute, therefore I want to talk to you. 

I met the Unstable on Purpose Dude on one of these apps and, after a few messages over the course of a few days, said yes to a spontaneous “hey, meet me for a drink in an hour?” message.  During one short bar date followed a few days later by one slightly longer brunch date (yes that’s right, two-ish dates already with Unstable on Purpose Dude) I learned several things about him.  He was working for a super popular social networking company, but recently quit to do all the things he really wanted to do like travel the world, learn to sail, and become a master scuba diver.  I also learned one very important thing about myself – maybe I’m getting too good at speaking my mind with men and perhaps the pendulum has swung a little too far in the “I say whatever’s on my mind” direction. 

After knowing him for merely a few hours, here is what I said out loud to the Unstable on Purpose Dude: 

“I’m writing a blog about dating, so I’m probably going to write about you.” 

"I put ketchup on my eggs, does that gross you out?" 

“You are kind of the perfect guy, but you sort of seem unstable.” 

“Are you ever going to go back to work?”

 “Do you use a top-sheet?  I hate it when guys only use the bottom sheet – they come in a set for a reason!” 

To my credit, here are some of the questions I wanted to ask but didn’t:

“Do you have health insurance?”

“Did you have a near-death experience that caused the rapid-fire bucket list activity?”

“What are you looking for here? Because most chicks I know aren’t going to be cool with a dude that is only around half of the time.”

And the big one that I will never ask but am dying to know:

“How exactly are you funding all of this action packed, adventurous, spontaneous life living?”

Unstable on Purpose Dude is now bucket-listing on the West Coast for a few weeks (another unasked question “You have apartments on both coasts, how does that work?”) so who knows if I will ever see him again.  He is an interesting dude though and – if nothing else – has inspired This Dater to start doing some of the things I’ve been putting off.   Don’t get too excited… buying a set of watercolor paints was as adventurous as I got this week.  Actually using them will be next week’s thrill.   

A Tribute To My First Mini-Relationship

As it turns out, This Dater went from dating to a full-blown relationship pretty quickly.  This Guy and I ended up spending more and more time together, had the “are we exclusive??” talk, left a toothbrush at each other’s apartment, and even spent a weekend away together.  There were so many wonderful things about This Guy and I learned a lot about what a relationship can be like.  In the end, This Guy felt better as a friend than a boyfriend, so that was that. 

A few lessons learned:

Nice guys do exist.  Nice guys give compliments genuinely, not just because they want to get into your pants.  And the best kind of compliments are about who you are as a person, rather than what you look like or what you are wearing.

Being honest with your feelings is pretty cool.  There were several times with This Guy where something didn’t sit right with me and I said it out loud to him, instead of holding onto it or complaining about it to one of my friends (truth, so there was still some complaining to the friends - progress, not perfection!).

Expressing your feelings doesn’t mean you always get what you want.  Sometimes it went like this - - Me: “Hey This Guy, it bugs me when you do blah.”  This Guy: “Oh ok, I’m sorry that bugs you, but I’m probably going to keep doing blah.”  Relationships are about deciding what blahs you can live with, and what blahs are deal-breakers. 

Breaking up with someone is hard.  Deciding to end things with This Guy was difficult, and actually ending things took longer than it probably should have.  He was my first taste of really nice and really into me, and part of saying goodbye was dealing with the fear of “what if I never find someone like This Guy again.” 

The only person who can validate you is you.  Within five seconds of ending things with This Guy I had called, emailed, or texted three people for support.  “Tell me I’m not a bad person.” “Tell me I did the right thing.” “Tell me I won’t be single forever.”  Even though my support people said the right supportive things, I had to come to grips with the fact that I did what was best for me, and there ain’t no shame in that game.    

So what’s next for This Dater?  More dating!  I learned so much during my mini-relationship with This Guy, not just about what I want and don’t want in a future partner, but also about areas I still need to work on.  I’m excited to get back out there again and continue learning and living This Dater's Life.  

Sometimes I Date Slow, Sometimes I Date Quick...

Before I sat down to write, I was thinking this was going to be all about how slow sometimes things move in the early stages of dating, and how grateful I am for this slowness even though it’s kind of annoying.  But the truth is it has been a little over a week since my last post and I’ve seen This Guy twice, so I guess things aren’t actually going that slow.  Perhaps I’m used to warp speed  (followed either by crash and burn or by instant relationship) so maybe this – seeing each other once a week – is “normal.”  Maybe getting to know someone by talking to them instead of getting to know the inside of their mouth through a booze fueled make-out session is the way to go.  Maybe going back to your respective apartments alone after a goodnight kiss rather than awkwardly having to say “um, I have an early meeting, but I guess you can sleep over if you want” is a perfect way to test out if you actually want to see someone again, and to find out if they want to see you again. 

Here are the annoying parts about going slow.  The time between dates – even if only a few days – can feel like a century.   Because I am a woman and even my best efforts sometimes result in a pit stop in crazy town, a few days of slow dating can result in a downward spiral of overthinking… “Do I still like him… does he still like me… is he dating other people… is it ok that I don’t want to date other people… kissing is nice but what if I want a tiny bit more, what should I do, what should I DO!!!?”

And here are the good parts about going slow.  I haven’t made any decisions so far that I regret.  While it may be hard to wait for stuff to happen, I have not left any date with This Guy having done anything I wasn’t 100% comfortable with.  Letting things happen slowly also allows for anticipation to build.  I get really excited about dates with This Guy.  We flirt and it’s fun.  I walk away from each date wanting just a little bit more, and wondering what will happen on the next date.  And – surprise, surprise – through all the talking, I actually know stuff about This Guy.  I know what some of his family traditions are, I know his middle name, I know what his dream job is, and I know some of the things he’s scared of. 

I do however think there needs to be a point when the slow dating picks up speed, once a week for a long period of time isn’t going to cut it for what I’m looking for out of a relationship right now.  I am also scared that slow dating has the potential to be a sure-fire road to the friend zone.  But because I can still count the number of dates with This Guy on one hand, I don’t think it’s wise to make that call just yet.

I hadn’t even realized this until just now, but my discomfort with slow dating may in fact be leftover garbage from my recent long-term relationship.  I’m used to having someone there all the time to call, not really thinking about what my weekend is going to look like, and not worrying about what kind of naked party would or would not be happening.  And this part of dating – this slow dating - is definitely throwing me off my game a little!  Just enjoying the dating ride is honestly something I thought I would be better at, or at least more prepared for.  But hey, going on dates, feeling that sense of anticipation, making out (which seems to disappear when dating turns into a relationship, am I wrong?), and most importantly having no regrets is something I can definitely be down with for a little while longer.  I’m not sure when I’ll be ready to move into the fast lane – either with This Guy or with someone else – but for now, This Dater is setting the cruise control to slow and steady. 

Take That, 35!

Guess what has been happening in This Dater’s Life lately?  No dates!  But lots of life.  First things first, I turned my scary age, 35.  And no, I didn’t wake up with forty thousand new wrinkles and my reproductive organs did not fall out.  I spent the weekend with my mom in my “happy place” – a beautiful hotel in upstate New York.  I also coincidentally spent my 34^th birthday in this same place… alone – unless you count alcohol and chocolate cake as guests.  Having a birthday usually comes with a little reflection and to be perfectly honest, 34 was a pretty crappy year.  There was unhappiness in my job, in my relationship, were I was living, and just about everything else in my life.  And self-medicating through various addictions was my way of coping. 

The last few months of 34 started my healing process, but to me there is something about a birthday that makes things more official.  I feel so much happier and optimistic today – at 35 – than I have felt in years.  35 no longer feels like my scary age, it just feels like MY age.  And damn it, 35 is going to be MY year.  It’s not that I think 35 is the year I’m going to find true love, get my dream job, or fulfill all my hopes and dreams.  What I mean is that 35 is the year I’m in the driver's seat, I get to make decisions that contribute to my happiness, and say no to things that don’t.  And if there happens to be career success or love along the way, well that’s just great.      

So what does This Dater do when not dating?  I live!  This week I re-joined a book club after a few month hiatus.  I was hesitant about returning because – while all of the women I had met previously are wonderful – the book club was more about wine than discussing a book.  Once again I learned that I can participate in social situations where drinking is a presumed natural activity and not drink.  And once again I learned that no one seems to care or even notice.  When I think about it logically, if the situation were reversed and I was in a group where someone said, “oh no thanks, I’ll just have club soda,” I would probably be like, “cool, whatever,” and not like, “OMG what is wrong with you!  Don’t you like to have fun?  Are you an alcoholic!!!???”

The other thing I did this weekend had nothing to do with tempting situations, but did produce some pre-activity anxiety.  A few weeks ago I signed up for a volunteer organization called New York Cares, which is a platform for bringing together hundreds of different types of activities all around the city.  My first activity was yesterday – helping Autistic kids with arts and crafts.  I have no experience with Autism, so I wasn’t sure what to expect and I was nervous.  These kids were more amazing and inspiring than I could have ever been prepared for.  It’s true what they say about volunteering – you often walk away having received far more than you’ve actually given. 

Wondering what’s on the agenda for This Dater this week?  Me too!  Another volunteer activity on Wednesday, this time helping women that live in a shelter do some beadwork and jewelry making.  And Friday night is foreign film night with book club women.  Other than that, maybe a spin class?  Maybe some yoga?  Who knows.  But what I do know – I’m 35, this is MY year, and I get to do what I want!  

My Journey Back From The Crazy.

A few facts:  I’m a woman; women sometimes act crazy; I went a little crazy.  Luckily I had my super awesome friend and the help of her super awesome new husband to talk me down from the crazy ledge.  We were talking about my last post (rant is more accurate) about the plan-ahead gene that seems to be missing from the male population at large.  She said, “I totally agree with you.”  Her husband said, “Maybe you’re putting a little too much thought into this.”  Interesting.  Turns out men do indeed know men best, and literally while this conversation with them was taking place, I got a text message from This Guy asking about our date for the evening.  The date was semi-planned on Sunday (i.e. “yeah, Wednesday sounds good!”) but because of the lack of time and place specifics, I was left scratching my head – are we going out or aren’t we?  If I venture into the scary land of male brain for a second, I’m guessing here is what he was thinking: “We agreed on Sunday that we were going out on Wednesday.  Now it’s Wednesday, I should probably figure out when and where and let her know.” 

So – Wednesday night was the first official date with This Guy, where both of us knew it was a date.  I noticed myself putting more thought into getting ready because 1) I like This Guy and 2) I knew for sure it was a date.  Side note, getting ready for dates is fun – picking out an outfit, putting on a little extra makeup and making sure my hair looks just right usually results in a little boost of confidence, which has the added benefit of calming my nerves just enough.  Add in the fact that it’s finally spring in New York and I no longer have to wear puffy coats and snow boots, and I usually walk into a date feeling like a champ. 

We met for dinner and just like the non-date/half-date, conversation was relaxed, easy, and full of laughter.  This Guy really makes me laugh, and I make him laugh too.  He’s just such a happy and positive guy, it’s different than what I’ve known in the past. I asked him if there was anything that made him mad – bullying was his answer.  Agreed – ain’t nobody got time for bullies.  Because I’ve know This Guy for a few months, conversation feels a little more in depth than what an average first date may include.  Past loves, family relationships, what we want for the future – it felt like nothing was off the table.

We ended the official first date in the same way the non-date/half-date ended, with a lovely little kiss - no homeless man serenade this time though.  Another thing I like about This Guy, he texts to make sure I get home safely.  Aw, sweet right?  I am pretty sure there will be an official second date with This Guy, but I’m going to do my best to make sure my last trip to crazy town was a one time thing, and give this whole process less thought in general (thanks super awesome friend’s husband!).  Oh, and speaking of what happens when you aren't stuck in your fog of crazy, News Guy and I have been in communication as well - we have tentative plans for next week (which I am actively not obsessing about, as of right now).  This Dater's Mama comes for a visit today, so no dates on the calendar for an entire week and plenty of time to not think about dating!   

The Mysteriously Vanishing Second Date.

I knew it was coming… dating isn’t all hearts and butterflies and giggly conversation.  It can be down right annoying.  I’m doing my best to let go of control, but I don’t understand why men have such a hard time planning ahead.  Or is that a sign that the people I’m interested in dating just “aren’t that into me” and some men actually do plan ahead?  They say they want to go out again, they text the next day saying “let’s go out again,” but then they don’t make plans to actually go out again.  What gives, dudes?  This isn’t just a one-man phenomenon, it happens nearly every time for me with every single date.  I guess if it happens again and again, then it’s really time to look at my behavior.  Perhaps I’m sending off some kind of “I say I want to go out with you again but I really don’t so don’t bother asking” signal. 

Here is my sure-fire-swoon-worthy dating advice to men everywhere.  If you like a girl, plan a second date!!  Like actually plan one, with a time and a place and say “does that work for you?”  “Ok, great, I’ll see you there then,” and then the day before, “looking forward to seeing you tomorrow” and then the day of you can even say “(silly anecdote about your day) and I’m excited to tell you about it in a few hours.”  For real, tell me, please, someone tell me, am I asking too much?  Is this just not the way it works anymore?  Am I supposed to be ok with this now that I’m in my thirties?  But what if I want a man who looks at his calendar on Monday and says “Oh goody, I’m free on Thursday night and I would love to take that awesome gal out on a date to my favorite spot.  Let me call her now and see if she’s free.” 

As of right now, I’m disappointed with both News Guy and This Guy.  And The Midwesterner, well, haven’t heard a peep out of him since date one.  UGH.  This Dater's Tuesday night is for the birds!