Thoughts on Dating an Older Man

Despite thinking that age was a dealbreaker, I went out with the 46 year old again last week.  Honestly, I had planned to tell him that I just wanted to be friends, but after a wonderful three hour conversation at an adorable little wine bar, I wasn't sure that I was ready to relegate him to the friend zone.

I realized that I've never actually dated someone older than me.  Recently, it seems like I've dated a string of men who are younger than me--and you all know how that has gone.  Make-up/break-up (who is finally out of the picture and out of my heart, thankfully), Saxophone Guy, etc, etc.  It's the entirety of my past dating life because none of these guys ever wanted to commit, and they all had insecurities.

But now, I've met the guy who is ready to commit.

Older Guy doesn't appear to play games.  He is not scared by honest discussion about the potential issues involving our relative ages.  He has laid out his cards on the table--he wants to get married, he wants to have kids, he wants to have it all.  He is not scared of my work.  He has stated to me that he wants to be with someone who has a brain, and finds it attractive that I have one.  He doesn't have the insecurities or fears that guys in their thirties have.  Older Guy's career is stabilized, his location is stabilized, and he is ready to meet and be with his life partner.

But now, despite being handed the entire package, I'm acting like a guy in his early thirties.

Is it the age difference that's really bothering me or am I just being a coward?  Am I really ready to move into a relationship that has commitment written all over it?  Am I ready to be committed?  Or am I still just a player?

Perhaps the very fact that I'm asking these questions says that I'm not ready.  For the first time in my life, I'm in a location where there's loads of single people to meet.  I'm going on a lot of first dates, and (though I don't like to think of it that way) playing the field.  There is definitely a small part of me that thinks...maybe someone with the same characteristics, but more age-appropriate, will come along.

But honestly, isn't that what most men in their early thirties are thinking also?  It's interesting, when I brought this gentleman up with the Brain Trust, they were equally divided.  Half said to go for it and half started thinking of guys they could set me up with because they felt dating Older Guy was ludicrous.  One of the guys in the "go for it" group felt that I wasn't going to find what I was looking for (commitment) in men my own age.

Interestingly, my family was also divided.  My sister felt that it was perfectly fine (which surprised me), but noted that there were lots of people in relationships with wide age gaps.  Furthermore, she went on to name three or four couples she knew of.

In a world in which even The New York Times does a feature story about how our generation is "delaying adulthood," is it possible that I may need to be with someone chronologically older in order to find a psychological equal?

After a lot of self-reflection over the past few days, I think ultimately, I can't permanently be with someone who is nearly a generation older than me.  I'm still on the fence about the commitment issue.  I feel like when I meet the right person, I will want to commit to them.  The fact that I'm on the fence may also be a clue that this isn't the right person.

So, the first dates continue...

The arranged date is coming up this week--I'll report back.

Here's the Times article:
"What is it About Twenty Somethings?"  New York Times, August 18, 2010:
http://www.nytimes.com/2010/08/22/magazine/22Adulthood-t.html?_r=1&scp=3&sq=adulthood%20twenties&st=cse

Dealbreakers and Red Flags

I'm a huge fan of 30 Rock and think of Liz Lemon as my personal hero.  Remember that episode when Liz Lemon starts an offshoot show called "Dealbreakers?"  I feel like I've been living my own version of that.  Why, oh why, is there always something?

As I intimated in my last post, I recently went on dates with two very, very different men. 

The first guy was a saxophone player I met recently while performing...in a square.  Yep, it's slim pickings and I was picked up by a street performer.  That being said, he was actually a trained jazz artist and we had a lovely conversation after his performance.  The conversation was so pleasant, that I agreed to give him my number.

We went out on Sunday evening for a walk in the park.  We had absolutely nothing in common except for a shared passion for our very different sorts of work.  However, he is barely scraping by, but I am on the brink of realizing my dreams.  At one point, he stated that he wanted to kiss me, but he had recently kissed another girl and felt bad about wanting to kiss me as well.  Needless to say, red flags were going up in my head, but did I heed?  Of course not.  So we kissed, and it was nice, and then I found out he was in his late twenties.

Too many red flags...financial insecurity, multiple women, late twenties.

Dealbreaker.

Next.

The second guy was an English bloke I met at a pub downtown last week.  Sexy accent, cultured, great dresser, stable job...but seemed a bit older.  He gave me his number, which I thought was a bit odd and maybe old school.  I have a rule about that--I don't call boys.  After not calling for a day, he managed to track me down via social networking, and I relented (just slightly) and emailed him back.

Despite the red flags in my head, we went on a date on Monday.  It was one of the best dates I have been on in awhile--the wine flowed, as did the conversation for several hours.  I finally worked up enough liquid courage to ask him how old he was...totally thinking maybe late 30's...nope, 46 years old.  Divorced.  No kids and unlikely to want kids.

Fifteen years my senior (citizen).

Dealbreaker (with hesitation secondary to the great conversation and otherwise excellent connection).

Er...do I even want to know what's next?

On the one hand, my work didn't intimidate either of these guys.  On the other hand, with each date that I go on, the list of dealbreakers is expanding like the American waistline. I worry that pretty soon all that will exist in my head are exclusion criteria and there will be no inclusion criteria.  Guess all I can do is continue to charge onwards and upwards...

An Update: The Game

Oh boy(s).  SingleFemaleSurgeon's life has been interesting lately.  Here's an update on the latest happenings.

First, an update on The Game.  I've made it about halfway through the book as it can really only be tolerated in small doses.  Much to my chagrin, I think the member of the Brain Trust who felt I shouldn't read it because it would make me jaded was right.  It's hard to go out, meet men, and constantly wonder if they're just running Game.  Are they actually interested in SFS, or are they just trying to get into my pants?  Yeah.  Ugh.  This has led me to wonder if love exists anymore, and if it does, if it's in the cards for me at all.  Yeah.  Ugh.  Again.

Due to this ridiculous feeling of dejectedness and then the accompanying panic at the thought of being single for the rest of my days, I am embarrassed to say that I grudgingly accepted a face-to-face date with Arranged Dating Guy who lives in the Western Time Zone.  I am meeting him in nine days.  I made reservations at a local hot spot I've been wanting to try, and the Brain Trust is on call to rescue me from death by boredom.

Somehow, with a little help from my friends, I have managed to scrape myself off the floor of dejectedness/panic.  Instead of continuing to freak out about external issues, I decided to concentrate on what Neil Strauss calls "Inner Game."  This is probably the only useful and moderately non-perfidious portion of the book.  "Inner Game" is the process of self-improvement.  So I threw myself into work, talked to family and friends, worked out a lot, and read.

Finally, I felt like rejoining the human race and actually went out.  I recently have met two very very different sorts of men.  Update to be continued...

u r nutz

The other night, I thought I met someone nice, interesting, and well-adjusted.  We had a few beverages, talked, snuggled.  I thought it all went swimmingly.

Then, the next day, I got a text message from him:

u r nutz

Aside from the utterly annoying lack of grammatical decency, I was floored by the bluntness.  What on earth does this mean?  And why, oh why, would you ever say that to someone you barely know?

Then, I started to wonder if maybe he was right.  I looked over the blog posts from the past nine months, and the ridiculous cemetery of my past relationships and recent dates.  Why do men think I'm a project?  And why do they make these snap judgments?  Is this some new pick-up scheme?  The extreme "neg?"

I started to wonder if maybe there was something to this text message.  Maybe I am actually crazy, I don't have the insight to realize and fix it, and that's why I'm still single?  I started frantically Googling DSM criteria and diagnoses like a first year medical student.  Did any of the diagnoses fit me?  Oooh...maybe I have a personality disorder?  Borderline?  Narcissist?  Avoidant?  Or, rue on me, maybe antisocial?

After a little bit, I calmed myself down.  We all have issues, quirks, baggage--even this Nutz Guy.  Especially after the trauma that is nearly fifteen years of delayed gratification, schooling, and residency.  We also have our ups and downs.  We all have insecurities.  And even in a huge new city, in a profession in which we are constantly surrounded by people, we can still be lonely.

I let the text message get me down for (embarrassingly) several days.  Then, I decided to let it roll off my back.  I don't think I'm crazy, but a little self-exploration is a generally healthy thing.

But I won't be seeing Nutz Guy again.  Or maybe I'll reconsider, if he starts spelling out his words like a normal person.

Intimidating Jobs

What defines a job so intimidating that members of the opposite sex actually run away when you mention it?  Or, what defines a job that is so sexy that members of the opposite sex actually think you're more attractive because you have it?

Once, a couple years ago, I was out at a bar with several of my friends.  One of the (male) friends of my friend came up to me and started a conversation.  It soon became apparent (even to clueless me) that he was flirting.  He was cute and I was game, so I started flirting back.  Then...he started asking me questions about what I do:

Him: What do you do for a living?
Me: Er...I'm a doctor.

(Doh! Strike One)

Him: What kind of doctor?
Me: Er...I'm a surgeon.

(The look of fear on his face was priceless)

Him: What kind of surgeon?
Me: (Major hesitation here) I'm a urologist.

Him: I would be SO intimidated to go out with you. (He says as he turns and literally runs away)

The guy could not get away from me any faster, and I have had many subsequent experiences that are eerily similar.  I still have too much pride to say that I'm anything other than I am.  I worked damn hard to get here and my job is a good weed-out process.  After all, I would never want to be with someone that insecure.

The other night, after an evening of drinks with friends, I hopped into a subway station and started to head home.  I ran into a couple guys who thought I was following them in the subway tunnel, and we started chatting because I love random conversations.  Eventually, it turned out that they were just getting ready to go out and invited me to join them for a drink. 

I hesitated.

Random dudes, random subway, big city.  They seemed genuine and nice, but don't all axe murderers?  They implored, but I still hesitated.  So, I asked them what they do for a living to stall.  Then they hesitated.  They didn't want to tell me what they did for a living because they thought I would be intimidated by what they do! 

Well, this certainly struck a chord with me.  I eventually got them to tell me what they do--they were firefighters.  The guys were worried that I would only like them because they were firefighters, because what girl doesn't want to date a firefighter, right?

I went out for a drink with them, and had a blast (no pun intended).  The best part?  They were so unimpressed with what I do for a living.  I guess if you're jumping out of burning buildings every day, being a surgeon is just a tad bit drab.

The Game

Okay ladies.  This is not for the faint of heart, as I am slowly learning. 

I mentioned "The Game" in my last post.  The Game is a book written by Neil Strauss that details a secret society of men known as the seduction community.  It describes artfully how to pick up women anywhere, anyhow with various not-so-nice-guy tactics.  There was a New York Times article by the author:

http://www.nytimes.com/2004/01/25/style/he-aims-he-shoots-yes.html?pagewanted=1

See anything of Three Downs Guy in here?

Yesterday, I perused the catalog of my local big city library to find a copy of the book.  Shockingly, there wasn't a single copy available in my entire huge Eastern Time Zone city for check out, and there were multiple holds.  However, I did find a copy of Rules of the Game by the same author which was surprisingly at my neighborhood library.  So, I headed over there, feeling like I was on some kind of quest.  I looked under the call numbers...no book.  The library was pretty small, and I searched it up and down.  The librarian assisted me in my quest.  No book.  We spent half an hour looking.  Amazing how it said it was available, but was nowhere to be found.  No metaphor for dating life there.

However, I was able to get a copy of the original The Game from the (female!) S.O. of a friend.  Now, it sits on my bedside table, and I have to say, I'm a bit nervous to open it.

I was discussing this little journey with my guy friends (a.k.a. The Brain Trust) over coffee yesterday morning.  In an interesting twist, some of them wanted me to read it and some of them didn't.  I almost felt like they were fighting for my soul.

In the "pro" argument, The Brain Trust felt that reading the book would be empowering and I could be privy to the not-so-good-guy tactics used by not-so-honest men to pick me up.  In the "con" argument, The Brain Trust felt that good guys who need help with approaching women would be blocked too.  So, this all comes to a sensitivity and specificity question.  Do I read the book and use the knowledge to block all men who try it on me, with the knowledge that I might lose the opportunity to meet a few good guys in the process, or do I just let it all play out knowing that I could get hurt by a bad guy?

Unfortunately or fortunately, I can't resist the apple of knowledge that is sitting on my bedside table.  Here goes...with a heightened sense of trepidation.