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

SFSingleGuy – The End

This week is the third and last part of SFSingleGuy’s story.  In case you missed it, I started something new here on the blog a couple of weeks ago.  I’m going to have guest bloggers on Sundays.

If you missed parts 1 and 2 – they can be found here and here.

“You’ve got mail!

We didn’t go out that next week, instead talking over .  I’d call her and leave a voicemail, and would get an in response.  Work had gotten really hectic for me over the past few weeks, and she was stressing because her company was in talks to get bought by a much larger European rival.  So the week went by pretty fast, and then I gave her a call again on Sunday, hoping to talk to a real person but got voicemail again.

I got her email the next day on Monday.  It asked if I wanted to take a break from dating, saying that it seemed like I had been really busy with work lately (I had).  I was kind of floored, I knew things had slowed down but I didn’t realize they had gotten this far in her view.  I wrote back that I did want to keep seeing her.  We made plans to meet up on Wednesday for dinner, and that week things kind of seemed back to normal.

Things seemed to go well for the next couple of weeks, but I was still working a lot.  I had been trying to finish up a product that I had been developing for about six months, and was mainly working at night until 3 or 4 am every night.  So the next week when we did our Wednesday date, we ended up in bed around eleven after some cardio fun.  The problem was, I couldn’t fall asleep, and was so restless that I was keeping her up.  So I volunteered to go home so that she could get some rest.  She joked about ‘just leave the money on the nightstand’, and I thought that was funny, but it was one of those things where I wasn’t totally sure.

We were coming up on three months, and I knew that I would have to make a choice where I wanted this relationship to go.  I was having a really hard time figuring this out, because I didn’t really have a frame of reference; I had never been in a relationship three months in a row (as opposed to years off and on).  I thought about this issue a lot, and decided that I should go out on a date with someone new to get a frame of reference.  I thought that I really did like this girl, but I needed to be sure before making a commitment.

So I got back on the dating site (luckily the other people can’t see your activity), and I found a new girl and started communicating with her.  I was having a hard time reconciling what I was doing with my conscience, but I knew that the end would justify the means.

In the meantime though, L (the girl I was currently dating), had to go to London on a business trip, and asked me to go with her.  That threw me for a loop; I actually couldn’t pull off a short trip like that with my current workload, but it gave me some reassurance that she hadn’t written me off yet.  When she got back, she asked me to go to a party that Saturday for some of her coworkers.  She wasn’t that comfortable there, I could tell, but I don’t think it was because of me.  I was able to chat it up great with the hosts and everyone else.

On Monday I went out with the new girl A.  We met up at a wine bar; I was nervous and I’m pretty sure that it showed.  She was a human resources VP at a company that had gotten acquired and had been a competitor of a company I used to work for, so we had plenty to talk about.  She told me that she would text me the next day when we parted, but I knew that she wasn’t interested, I was out of her league.  I had kind of forgotten how much work dating new people was, and was kind of glad to have a great women I was currently dating.

Having gotten my frame of reference, I decided that I would want to give a shot at taking things further with L.  I called her the next day, and we talked briefly over email that week as I worked on planning a date for the three month mark.  Work was still crazy for me that week, and things got away from me, so on Sunday I ended up leaving her a voicemail again.

Monday came and work quickly ate up half the day.  Around 3 pm I got an email from her.  “I think you’re a great guy, but I really don’t think this relationship is going where I want it to”.  Oh, and that stuff about wanting to be friends still.

Bang.  I almost fell out of my chair.  I called my best friend’s wife who I was good friends with, and asked her advice.  She said give it 24 hours, then write back that I’m sorry that I was being proactive enough, and wanted to give it another chance.  So I waited 24 hours, and replied to the email.  And I gave it 24 hours after that.  And I didn’t hear back from her at all.  Dumped by email.

Over the next few days I suffered some acute loss of self worth, but I wasn’t broken hearted.  Did I really want to be in a relationship with (or friends with, for that matter) someone who dropped me over email?  I had sensed red flags here early on in the relationship with the “I call, she replies by email” pattern that had established.  Communication is hard, and I think communication between men and women really requires each side to try and speak the dialect of the other.  Conflict is hard too, and I felt like L had skipped over the conflict phase and gone straight to , or at least kept me out of the conflict.

I took some time to reflect on where I didn’t measure up too.  I hadn’t made time for the relationship when I should have.  I hadn’t stayed the night over when she needed me.  I read her signs, and didn’t always realize what they were saying.  But I don’t have any regrets, I had a good time, and I’m pretty sure she did too.  And now that I’m single again, I can take those things I learned, and work on applying them to a new frame of reference.”


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3 to “SFSingleGuy – The End”


  1. Anonymous says:

    He went out with another woman so that he could figure out how he felt about his girlfriend? I don’t understand men.

  2. sfsingleguy says:

    Yikes; reading this again, I saw an error. I meant to say that A was out of my league. Puts a different twist on the story; sorry for that error.

    @Anonymous – L wasn’t officially my girlfriend; as far as I could tell. I was hoping that was going to happen, but it didn’t. I’ve been in situations where I assumed that was the case, but it wasn’t. And that is an unpleasant situation to deal with when you find yourself there.

  3. Nancy says:

    I’ve been reading this blog for a little over a month now. Randomly came across it and as is my way: when I fall in love with something (in this case, this blog) I have to obsessively read it. Starting with post 1 I’ve been working my way toward present day. I swore I wouldn’t comment until I was current because it’s probably lame of me to go back this far but I just had to.

    First, I love the idea of guest bloggers and love that the first was from a guy. The story offers a perspective we with vaginas rarely get to hear/read since most breakups don’t involve a debrief. Kudos to SFSingleGuy for being reflective and learning from the relationship. Very refreshing!
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