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

Lawyer, Lawyer, Lawyer

I have a couple of special treats for us today.  It’s Sunday, so that means we get to enjoy another Guy’s Story.  I was blessed this with week by having two great guys submit their stories, so I decided to use them both, rather than hold on to one until next week. And hey, if any of my male readers are interested in contributing please shoot me an email –

This morning we have another great story by .  I’ll publish the second story, by a new contributor, later in the day.

“In , sometimes you find forumulas that work.  I’ve heard from some women that they always click with doctors.  For me, a pattern has emerged; I click with lawyers more often than not.  I spent the first three months of 2009 a lawyer.  When I looked back through my past relationships, the ones that seemed to have the sparks have always been with lawyers.  I don’t quite know why, but some of my friends have told me that because they think I’m smart, that it might be the meeting of minds that makes it happen.

Being newly single and back on the dating circuit, I had a date almost two weeks ago with a ‘do-gooder’ lawyer.  She worked for a law firm that specialized in going after large companies that screwed the little people.  She was attractive and smart, we met up at a bar for a drink on a Monday and ended up playing in the Monday bingo game there.  It wasn’t an uncomfortable date, but it wasn’t great either.  We were alike intellectually, but didn’t have much else in common.

At the same general time, I had been chatting up another lawyer on the chemistry dating site.  I felt somewhat of a connection there, and asked her out for a glass of wine.  We were both busy that week, and I had a bike ride that weekend, so we left it to get in touch after Memorial Day weekend.  Her dad was in town the week before, and I was in seclusion mostly preparing for my ride.

Fast forward to last Thursday before Memorial Day weekend; she left me a message on the dating site saying next Thursday (a week ahead) would work.  I was surprised; I wasn’t sure if she was playing it cool or was genuinely interested.  I wrote her on Monday (Memorial Day) confirming the date and venue, and then heard back from her on Tuesday.  She left me her number, and things were set.

Taking a clue from reading this blog, I texted her 24 hours before saying that I was looking forward to seeing her, and she responded in kind.  So tonight I hopped in a cab at 6:40 pm, and headed to the Mission District.  Got a text from her around 6:50 saying she was there, and in the back of the bar/restaurant.  I texted back that I was in a cab and would be there in about five minutes.

I found her easily, a quite attractive woman who was easy to talk to.  She had gone ahead and arranged with the host to get us a table, which I said was great.  Five minutes in, she mentioned that she had to leave around 8:30 pm to go and be the subject of a life coaching by her friend in front of a group.  She apologized that she would have to leave ‘early’, but I figured 90 minutes gave me enough time to figure out where this would go.

She dropped a comment about “I hope you don’t think I’m crazy”, but I can’t remember what that was followed by.  She was talkative, and I chalked it up to nervousness.  I got the standard barrage of questions that I always get when I go out with lawyers; I was prepared for this.  She apologized at one point for “being nosy”, but I think that is part of getting to know someone.  Maybe I looked a bit uncomfortable, but I thought I was smiling a lot.  I may have been a bit tired looking, I was on the bike for 10 hours a week ago, and was still recovering.

We got a table, and looked at the menu.  She asked my opinion, and I said the ahi tartar looked good.  She clapped and smiled, then said that was a girl clap, and broke it down for me.  I took that as having passed a test, and thought I was doing pretty good.  We started talking about families, and she brought up her brother who had dropped out of high school.  I mentioned that he was probably pretty smart if he was bold enough to do that, but I don’t think she thought of him favorably.  She complained that he was smoking pot all the time, to which I didn’t really respond; I partake occasionally, but I figured since I run two businesses and work my ass off, I have nothing to apologize for.  I did mention that I got an F my first year of college, which I think she didn’t react well too.  But I followed that up with telling her I was somewhat of a late bloomer, and had done really well later on.

She worked for a federal judge as an aide, so I sensed there might be some differences there in our views.  Although we had both talked about seeing live music shows, and while we were at the table I mentioned that the music that was playing was the band she saw last weekend.  More points for me I thought.

She asked me if I was an engineer; I said that I was previously, but was currently an entrepreneur, so I had “moved up a notch”.  She mentioned that her dad was an engineer, so I may have lost some points there, but despite the fact that I make sales calls, I still consider myself an engineer at heart.

Then came the question.  “So, do you have any plans for this weekend?”  I’d been working hard all week to make a big deadline yesterday, and I hadn’t set anything up for the weekend.  I remembered specifically at that moment that she had asked me on the dating site what I had learned from a previous relationship, and I responded “Always have a plan, even if it turns out to be a bad one”.  I answered truthfully; no, I didn’t have anything planned yet.  She had plans on Sunday to meet up with a friend in Monterey.  I knew I had blown that one.  Quick, what do I do?  I decided to play it cool.

We split the check, it was $20 each.  I wrote in 5 as a tip, but then remembered she had been a waitress, so I wrote over the 5 to bump it up to 6, and left my receipt in there next to hers – she had gone to the restroom after we gave our cards to the waitress.  I have no doubt that she saw my tip, but wondered what she would think of my 6 written over 5.  Hopefully something good.

We walked out, and I said I was going to catch a cab; it was a three mile walk from the mission, and despite the fact that I like walking, I didn’t mind treating myself to a cab.  She hailed me a cab, and did it well.  Do I ask her for another date here?  Won’t that look desperate?  What if this “life coaching” she said she was going to was really another date, and I was getting double booked?

I decided to play that cool also.  I had her phone number, and she gave me a hug before I got in the cab.  Should I text her on the way back while I was in the cab?  Could be bad if she was heading off to a second date, or even if she was going to meet her friend.  While we were standing there waiting for cabs, she asked me if I was going back home to work.  I answered no, which was mostly truthful.  I needed sleep, I had even taken a nap today so I was fresh for the date.

So here I am, trying to come up with a plan.  Do I call her tomorrow and suggest a date on Saturday?  Do I text her later tonight?  (my gut says no on that one).  We had played it pretty cool over email, so I figure I won’t screw up by waiting until the next day.  Writing this, I realize that I must really like this girl.  Now I just need to come up with a plan.

I texted her the next day at 12:30 pm, and got a response at 4:30 saying have a great hike.  No counteroffer.  That was it, but I’m ok with that.  Gotta keep moving forward, there will always be bumps in the road.

(Fast forward one week)

week, no counteroffer.  I didn’t make an effort to contact her again.  Her response to my followup up text said no thank you with frosting.  But I did have a first date with lawyer #5 tonight.  “Keep your eyes on the road son, and don’t look back”.

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7 to “Lawyer, Lawyer, Lawyer”

  1. flipper7809 says:

    It’s refreshing to be reminded that guys have the same dilemas as we do, text vs no text, waiting vs not waiting, play it cool vs being proactive. Dating is hard work!!

  2. pansophy says:

    Women and their checklists. Yuck. IMO, you should feel lucky you didn’t have to endure another evening of that.

    Not sure why being truthful is so underrated. It may not get you a second date, especially with a checklist person, but it goes a long way if you want something more than dates…

  3. sfsingleguy says:

    @flipper7809 – I don’t know many of my friends who don’t have these dilemmas, but I do know some of them who won’t admit to having them.

    @pansophy – Men have their checklists too. I can understand the motivation behind the checklist, but I think that sometimes it gets in the way of getting to know someone like you mentioned.

  4. Simone Grant says:

    The main reason I do this Sunday, Guy’s feature is so that we can see that in so many ways we really are the same. I’m so lucky to have brave guys like SFSingleGuy who are willing to share their stories with us.

  5. mrstoad says:

    I have enjoyed reading these Sunday stories, but in all honesty, if a guy splits a bill with me on a first date, there is no way, no way I am going out with him again. (Even if he is a generous tipper). I am happy to pay for the 2nd date, and I will gladly pay for the first (although in that case there won’t be a 2nd date), there is something about going Dutch that always sort of weirds me out. If you’re dating, I don’t believe in splitting checks. Someone always takes care of the tab and I never mind of it’s me EXCEPT on the first date.

  6. sfsingleguy says:

    @mrstoad – Figuring out how to handle the bill is one of the hardest decisions I have to make on a date. If I go out with six different girls, two will want to split the bill, two will want to pay, and two will want me to pay. Of the ones that want me to pay, half of them will be offended if I don’t offer to pay. Of the ones that want to pay, half of them will be offended if I offer to pay.

    This isn’t a big deal if it is a small date, I always offer to pay in that case. But if I go out with someone on a first date and the bill is $50 or $100, then the dynamics change. If I go out with a woman who has a serious career and works a lot, they usually are the ones who offer to split the bill, and if I try to insist on paying, they insist on splitting it and I feel like it is rude to force the issue. I also like being in a situation where I feel like I’m an equal with that person, but that is my own personal taste.

    There’s also the issue of you aren’t sure if the other person is offering to pay because they don’t like you, so they don’t feel obligated to go out with you again – I’ve had that happen. And then there are the cases where if you insist on paying, you are viewed as an old school misogynist. So after many dates, I feel like this is still an area that I get wrong most of the time.

  7. Simone Grant says:

    Who pays is such a complicated issue (who pays). I feel like the “rules” also shift depending on age and location.