Dating Life of a Thirty Something

Do you want an inside glimpse at a dating diary of a thirty something?  Someone shared her diary with me – and asked me to blog about it.

Occasionally, I get a private message from people I know – women and men – who are single and read my blog asking me to write about their experiences.  Recently, I got a message from a random acquaintance stating that every time she reads my blog, it is a reminder to her as to why she is still single.  Her exact words were, “I always think maybe it’s me, maybe I am doing something wrong.  But I know it’s not me.  It’s just impossible to find a decent guy who you are compatible with and who is looking for more than just sex.”

Boy do I know what she means.  I’ve been called a serial dater in the past.  I’ve analyzed my own dating experiences over and over again.  How do some people just seem to fall into relationships after barely just getting out of one?  I’ve been trying for four years, and I can count on one hand the number of guys that have turned into a second date – never mind beyond.

Some friends tell me I am too picky.  Others have said I’m going for the wrong type of guy.  That’s definitely not the problem – I’ve tried more fucking flavors than a Baskin-Robbins.  From plumbers and electricians to bank executives, and even a doctor or two.  From early 30s to late 40s.  Married and never been married.  Kids, no kids.  Five miles away to 50 miles away.  I’ve taken my chances on every popular dating site, even the ones I’ve had to pay for.  I’ve met people through mutual friends.

I even still talk to some guys I’ve been out with where the chemistry may not have been there, but we were both mature about it and randomly say hello.  And they are good guys so the fact that we still communicate on occasion tells me I must be somewhat decent and normal.

So here is the low-down on this woman who shared her dating diary with me.  I know her mostly through mutual friends, and have even hung out with her a few times.  Early 30s, attractive, college educated, and totally down to earth.

So here is her dating diary over the last six months, with notes included.  Out of 20, she only went to a second date with three, and never to a third date.  

  1. Brian, 33, Real Estate Agent — Crazy, didn’t understand social cues, truly thought he was going to kill me.
  2. Joe, 34, Financial analyst – Very nice, no real chemistry (contacted me months later apologizing saying that he wasn’t really ready to date when we met)
  3. Dan, 35, Banker – Really awkward, took 2 hours to drink a single beer, ate like a bird, loved musicals and The Golden Girls.
  4. Brian, 32, Golf Pro – Nice, cute, boring
  5. Noah, 34 (Occupation escapes me), Awkward, 30 min late for our date, put down exactly half of the check when it came. Reached out to me again 6 months later.
  6. Jon, 34, Tech Support Manager – Shorter than advertised, closed minded (extremely liberal and said he didn’t like anyone who didn’t share his beliefs), spit when he spoke
  7. Ali, 36, Police Officer – Aggressive, sweet talker, stopped talking to me after I wouldn’t sleep with him on the 2nd
  8. Peter, 32, Security Guard – Strange, lived at home with parents, obsessed with chick flicks and Disney movies.
  9. Billy, 32, Chauffer – Really sweet, thoughtful, no ambition, unsettled
  10. Jeff, 32, Bike Mechanic – Funny, sweet, honest, no chemistry
  11. Eric, 27, Government – Cute, funny, sweet, no real chemistry
  12. Patrick, 31, Teacher – Fun, lots of chemistry, disappeared
  13. Lee, 34, Accountant – Awkward, boring, criticized me almost immediately
  14. Joel, 37, (occupation escapes me) – Looked nothing like his pictures, walked with a limp
  15. Michael, 32, Carpenter – Irish cutie, sweet, smart, disappeared
  16. Jim, 32, Car Salesman – ambitious, smart, humble, lots of chemistry, disappeared
  17. Dan, 37, Software engineer – Cute, fun. Went on two dates and had a great time. Told me I was too nice.
  18. Nate, 32, Car Salesman (former baseball player) – Better in pictures, not a ton in common
  19. Sandy, 34, Robotics Engineer – Nice, polite, no chemistry
  20. Jack, 33, Sales Exec – Stood me up, five minutes before we were supposed to meet, he texted me something came up.

Is this not crazy?  I mean, think about it.  That’s about a date a week.  And this woman does not have children which makes her dating pool and flexibility even that much more than mine.  Out of 20 men she actually met in person, and not including the dozens she likely talked to who disappeared, and she can’t find chemistry with one.

I swear, the next person I hear say, “It will happen when you least expect it” will be choked.   Or for the married people I know who often tell me they “live vicariously through me” – does this look fun?

As this woman states, “There is nothing more I want than to find a great guy.”  I hear you, friend.  But as for how many of them are out there and not already taken, the odds are very bleak.  You might as well accept your fate like I have and get used to BOB being your only boyfriend.


Online Dating Diaries: When the Douche Comes Back

I have a very good friend who has been living the online dating dream with me the last few months.  She’s starting to become an expert at this in her own right, but every once in a while, I am still able to offer her a new insight.  “You were so right,” she’ll say.  I love hearing those words.

One recent insight I gave her was about a guy she had been on a date with where everything was great, including the chemistry.  Then the guy stopped texting her.  She was confused, but based on everything she had told me, I said, “Don’t worry, he will come back.”  And soon enough, he came back.  You know, the standard “Sorry I’ve been out of touch, just been SO busy.”

I told her to also expect the occasional random number to text her out of the blue.  You know, the guy you deleted from your phone three months ago who randomly texts you, “Hey, how’s it going?” and you’re saying to yourself, “Who the fuck is this?”  Well, that happened to her too.

It’s one of the truths about online dating I have come to realize:  many guys will come back.  Out of the blue, at random times, when you least expect it.  In fantasy land, a woman wants to believe that the guy is reconnecting because he is actually interested in her after all.  Maybe he went on a few dates with some not so great girls and said to himself, “That girl from a couple months ago was actually pretty cool.  Maybe I’ll see what she’s up to.”  It can happen, but don’t hold your breath.

REALITY CHECK:  They are coming back because they are bored and there are no other available options, or more likely, they are looking to get laid.  By pretending to actually CARE how you are doing, they hope you won’t be able to read through their disingenuous attempt at casual conversation.

So imagine my surprise when my douche of the century appeared out of nowhere after TWO MONTHS.   On the Hot Douche Scale, this guy was a solid 9.5.  It was probably safe to assume he’d fall into the Run Like Hell category, but in my dream world, I held out hope that he’d at least make it to the Dating Zone.

I connected with him instantly in one conversation prior to our date.  He said he had taken six months off from dating after getting out of a bad relationship.  I totally respected that as many people on the dating scene take NO TIME in between relationships for themselves to heal in a healthy way.  In fact, one recent date told me he had just ended a 5 year relationship three weeks prior.  He was a super awesome guy, and I gave him some parting advice, “Do yourself a favor and go have some fun.”

Now back to the douche.  This guy was an A+ in my book going in.  And when we met, the chemistry was instant.  Dinner was great, conversation was great.  We decided to take a walk along the river after dinner.  I had it in my head that I was totally going to make out with this guy.  I was even bold and said to him, “You know I’m totally making out with you.”  His hands were trying to go in places that were off limits which I quickly pushed away each time.  I can’t blame a guy for trying.  But within less than ten minutes, the mood changed in a mere instant when he said, “Can I get a blow job?”  My exact response, “Fuck no!”

This guy gets totally pissed and the conversation goes exactly like this:

Guy:  What you’re doing isn’t fair.  What you’re doing is actually worse than if you slept with a guy on the first date.

Me: Since when can’t you just make out and have fun.  I didn’t know that getting you off was a requirement.

Then he spewed the words that will be etched in my brain for eternity.  “If nothing is going to happen between us, then you can just bring me back to my car.”

So that was it.  Over, finished, done, finito, caput, done.  He went from an A+ to an F in less than three seconds.  My fantasy man turned complete cock sucker drove off, and I closed the chapter on that one.

Well, not really because HE CAME BACK.  He is THE LAST MAN I thought would ever reach out again.  He was long deleted from my phone when I got the infamous, “Hi, how are you?”  The actual conversation is below.

date comes back


Now to answer the ever confusing question:  Why do they come back?  You know why he came back.  I flat out asked him what he wanted.  He offered to bring a bottle of wine to my house, and we could “relax and watch a movie.”  TRUE STORY!!!  I obviously declined and he obviously tried to say he was just kidding.  But I have not heard from him again.

So the next time you get a random text from a phone number you don’t recognize, do not be fooled into thinking they really care how you are.  You are just one of many other random girls who received the same spam.  He is just looking to get laid – and you’re a fool if you give him the satisfaction.

Dating Diaries: The NHL Guy

What a more perfect time for NHL guy to reappear than during the Stanley Cup.  I met him last May.  He told me he was in the NHL, and I said, “Ok, and I’m a famous movie star.”  But I did my homework on him, and for anyone that knows me and what I do for a living, I DO my homework.  He totally checks out.

So after several weeks of conversation and texting and basically just playing with me, I laid it out on the line – either we are going to go out for real or he can go fly a kite.  And I pretty much said it like that.  He told me he was home for the season besides some random commitments and would have time.  So I get the random text one Saturday, fortunately on a weekend I didn’t have my kids, “What are you doing later?”  He said he had a golf tournament, but would touch base later in the afternoon.  So I get another text at 5:00, and he gives me a place and tells me to meet him in a half hour.  I was in the middle of a pedicure, and told him 7:30.  I’ll never forget the final words…

NHL Guy: Well maybe next time.

Me: Or maybe not…

Within two minutes, my phone rang.  And boy did I let him have it.  He tried using the “Do you know who I am” bullshit on me, and I said, “I don’t care who you are.”  I ripped him a new one for a minimum 15 minutes because I was so aggravated, and I will give him credit because he sat there and took it.

When he reappeared, I couldn’t believe he remembered me.  But he remembered things going down quite differently as you can see here.




You never know who you are going to meet when you’re out there dating.  We all tend to remember the bad stories, but we forget the good experiences.  NHL guy is not going to be my future husband, but he is definitely not a bad person to know.  When I meet good people, I try to stay on a friendly basis with them.  For example, the timing might not be right now, but you never know what could happen in six months, a year, two years.  They could be good professional contacts in the future.  They could have single friends who might be better for you or vice versa.

Above all, make sure you leave a lasting (positive) impression.



Join LinkedIn if You Want a Job – or a Date

I was somewhat of an early adopter of LinkedIn, having a profile up long before it became the premier networking site for professionals that it is today.  To this day, my online resume’ is not filled out with the exception of my work history and education, but that still does not prevent the occasional recruiter from knocking on my door with a job opportunity.  Nor does it prevent the occasional professional perv from reaching out with proposals for a date.  In fact, you might be surprised at how common it is.

I will never forget my first dating proposal via LinkedIn.  It was in 2007, and after returning from a conference in New York City, an attendee at the conference, who also happened to work at one of my organization’s largest banking clients, sent me a request to join my LinkedIn network.  After a few formalities, he casually mentioned that he traveled to Boston frequently on business.  He asked me if he could take me on a date the next time he was in town.  I had just found out I was pregnant with my second son at the time and thoroughly enjoyed telling him I was married with a three year old at home and another baby on board.  I wish I could have been there to see him crawl in a hole when I told him.

These casual proposals have continued randomly, but at least with the 2007 experience, it was someone I had actually met and interacted with directly in a business setting.  Today, the proposals are even more brazen and outrageous.  Some LinkedIn members are abusing the purpose of the site.  Besides just spammers, perverts and cyber stalkers were becoming such an issue, members started to complain which caused LinkedIn to add blocking features and other privacy controls just this year.  Have you blocked anyone yet?  I have.

Sometimes the scoping of potential dates may be done casually starting with actions such as unknown endorsers of skills to casual inquiries to discuss a business proposal.   For example, this past summer, I had one guy who I had a third degree connection with contact me as he wanted my “professional  opinion” on a new marketing tool his company was looking to launch.  In addition to my expertise, he blatantly stated that he would be interested in taking me out to lunch or dinner sometime.

In doing research for this blog, I learned that there was actually a dating app launched in 2012 called Hitch Me, described as a “safe, secure and reliable online dating platform for LinkedIn professionals.”  My first reaction, “Seriously, another damn dating site.  Are you bleeping KIDDING ME?”  But when I visited the page, I got this message.  I see that experiment was a real success.


This is a real problem, folks.  I have had numerous propositions fill my LinkedIn inbox and requests from people where I have no connections in common.  Then there are endorsements of your skills from people you don’t know.

A few weeks ago, I took it upon myself to privatize my LinkedIn profile which actually irritated me as it goes against the very purpose of what the site is intended for.  It’s a sad day when people are now using professional networks as dating sites.  Am I supposed to overlook the fact that you are old enough to be my father and instead be impressed that you are a VP at Citibank (yes, true story)?  Is that supposed to win you a date?  I think not.