Fearing Aggression

I’ve mentioned the girl I like in my office in a handful of posts so far and I think it’s time for a quick update.  Unfortunately, the update isn’t really about progress, it’s more about my own trepidation.  As I’ve mentioned before, the last time we went out, she ended the night by instigating a kiss.  It seemed at the time that there might have been something there.  But now I’m worried that maybe one too many glasses of wine may have been behind that kiss.

We left that night similar to the first night we went out.  It was a late Friday night and as I was leaving her I asked, “When can I see you again?” hoping that maybe she would be free on Saturday night.  Both times she replied, “Monday.”  Of course, Monday means “some time next week” as I it’s rare I would see her in the office on Monday and if I did see her, I would most likely just say a professional “Hi, how’s it going?” before receiving a one word response and moving on.  Fast forward to that Friday — I was hoping to hang out with her again, but she was busy.  I gave her a simple, “cool, well have a good Friday.  Let me know if you want to hang out on Saturday or if you friend ditches you tonight.”  No big deal.

The next Friday I was hoping to catch her after an early evening work party maybe to meet up for a drink or a bite to eat.  I actually had a handful of opportunities to grab her attention.  In fact, she spent a good 30 minutes or so working at a table near my desk — which she rarely, if ever does — and I wonder to this day if she was hanging out close to me hoping I might drop by and ask her out.  Though, I could be reading too much into it, so I opted not to approach her until later in the evening.  Unfortunately, by the time I worked up the gumption to ask her out, she had already left for the night.  I caught her on work Instant Message and she was already home.  Before I could see if she was up for grabbing a drink or something, she mentioned she was already lying in bed at 8 pm and was absolutely exhausted.  That was okay too.  She works very hard, which I admire, and I wasn’t about to be upset if she needed a Friday night for herself.  I signed off the chat with a similar, “Get some sleep! Let me know if you want to grab a drink or a bite to eat on Saturday or something.”  “Will do” she replied.  Of course, she never reached out.

Jump to the Friday of last week.  I was working a little bit late and was surprised to see her roaming around the area around my desk.  She didn’t drop by my desk at first, rather she sat down and talked with a co-worker for a bit.  Again, I could be reading too much into this, but it’s very unusual for her to be hanging around my area of the office.  After a while, she passed by desk and stopped in quickly to say hi.  Granted, I made eye contact with her as she was passing, so it’s possible she felt obligated to say hi.  I asked what she was up to this weekend and she said her good friend was in town visiting over the weekend.  Obviously I wasn’t about to ask her to ditch her friend to hang out with me and she didn’t seem to be inclined to invite me along to her St. Paddy’s Day plans.  She never inquired as to my plans.  I later found out a different co-worker was at the same party as her on Saturday night and he almost called me to come drop by, but he didn’t.  For those of you who read my post last week, I was considering asking her over on Saturday night and I would cook her dinner, but I wasn’t about to ask her that if she had a friend in town visiting from the East Coast.

In between these Fridays, we occasionally talk online, usually for 30 minutes or so right before signing off Instant Messenger and going to bed.  Often she instigates the conversations, which gives me signs of hope.  But, again, I could be reading too much into it.

A week ago, we had out annual sexual harassment seminar and the lawyer who came in to outline policy had a whole slew of examples of what constitutes harassment and what does not, often with real world stories.  A funny story he told was about a client who was accused of sexual harassment after he asked out a girl in his office 9 or 10 times and he “couldn’t take no for answer.”  Basically, the girl always had a lame excuse (“I’m washing my hair” … “my mom is in town” … “I’m meeting friends for dinner” etc) and the guy couldn’t take a hint.  Long story short, the charges were dropped when it became evident that she never actually said “no” to his advances, but was being polite white the guy was just oblivious to the fact that she wasn’t interested.

I wonder if maybe I’m like that guy.  That maybe the girl in my obvious isn’t actually interested and the two times we kissed were just because she was a little tipsy and not thinking straight at the time.  But then why is she chatting with me online? Maybe she’s just being nice.  Maybe she chats with a lot of co-workers.  So today, I’m afraid to ever be aggressive again.  I don’t want to be the idiot who can’t take a hint.  Over the past 5 weeks, I’ve gone out with her twice and “sort of” asked her out two other times, though they weren’t direct invitations to specific dates.  I really like this girl, I thought maybe she liked me too.  But maybe I’m reading signs that aren’t actually there.  Because I work with her, dating is a very delicate subject.  I don’t want to cross boundaries and I certainly don’t want her to file harassment charges against me (though I don’t think I’ve been that aggressive).

I think I’m going to tone down my hopes and leave things in her hands.  I hate doing that since I think a lot of girls prefer to let the guy do “the asking” even though they obviously don’t have to in this day and age.  And I generally don’t mind asking a girl who I think is interested in me.  But, again, I don’t want to be the oblivious idiot.  Hopefully I’m not passing up on a real opportunity here.


I had lunch with a friend at work today.  I’ve only known him for about 4 months (virtually my entire time here in San Francisco) but this was our first lengthy one-on-one discussion that managed to not involve any work discussion.  So, of course, we talked about the only interest we really have in common: dating.

I consider myself something of a hopeless (hopeful?) romantic.  I don’t necessarily think I’m anyone’s prince charming or a guy who’s completely devoid of sexist notions — though I do my best to avoid them.  I do think, however, that I’m in the minority of guys who likes all of the following: romantic comedies (When Harry Met Sally & You’ve Got Mail among others), holding hands, kissing in the rain, dancing at weddings, wine bars, a girl who gives good mind, cooking together (in a class or at home), sending her flowers, supporting her dreams and snuggling on the couch watching a movie or TV.  Okay, maybe none of that makes me a hopeless romantic, but it does make me cheesy.  Regardless, I tend to like girls who are smart, ambitious and compassionate.  While I’d be lying if I said that someone’s empirical attractiveness is not something that catches my eye, I simultaneously don’t need a girl to be cover-girl-gorgeous to fall for her.  In fact, I love getting to a point where it’s the minor flaws that I find most attractive about a person — eventually you don’t see empirical attractiveness, you just see the girl.  And seeing that girl will make your heart flutter even if she isn’t about to walk the Victoria Secret runway.

Okay, so back to lunch: my co-worker and I were discussing past longer relationships and girls we’d dated recently or flirted with recently since moving to San Francisco.  Out of no where he said something interesting, “I hate it when you find the perfect girl — except she’s just not attractive enough.  You know?  So close.”  I’m paraphrasing a bit, but it was something very close to that.  For him, a girl not being absolutely gorgeous is a big enough flaw to not be interested in them.  I clarified with him that she could be “average” looking and that wasn’t good enough.

In my interactions with this co-worker outside of the office, I’ve seen him be somewhat of a ladies man.  He’s managed to bring three different girls to four of the parties I’ve seen him at, which I suppose implies he’s charming or at least persuasive.  I’m an awful judge of whether or not a man is attractive, so I can’t really comment on that but I don’t think he’s particularly handsome (take that with a grain of salt).  He’s also not a “bad boy,” in that he’s an analyst at a tech start-up who doesn’t come across as a jerk when you first meet him.    So, I wonder, do girls realize that he’s prioritizing their looks above all of their other qualities?  I also wonder that if he were to ever marry a beautiful woman and then her looks faded if he would divorce her or cheat on her because her “most important” quality was no longer there?

I also think that part of his ability to pick up girls is just playing the odds.  If you approach enough girls you’re bound to get some yeses in the sea of nos.  And I wouldn’t say “he’s got game” either.  I’ve seen him try to pick up a girl in the bar and be literally pushed away for being too aggressive.  He was drunk at the time, so maybe he was just unaware of what he was doing, but I once saw him lean in to kiss a girl in a wall-to-wall crowded bar of 20-somethings and the girl had to push him away to make sure his lips didn’t make contact.  It’s the only time in my life I’ve ever seen a guy try to kiss a stranger so aggressively.

After he told me about his requirement that a girl is attractive, he expected me to sympathize with him.  “I don’t think I’m quite so superficial,” I replied somewhat baffled.  I couldn’t think of a more euphemistic word than superficial.  “Superficial?  I’m not superficial.  But you know what I mean,” he chuckled back.  I didn’t know what he meant.  He spent the rest of lunch showing me a dating app that I hadn’t seen in person called Tinder.   He showed how he carefully swipes through pictures of girls and only messages the attractive ones.

I suppose this is probably somewhat typical of both genders — to judge by looks first.  But I think both genders also have the ability and civility to rise above looks when looking for the right partner.  Our ability to be attracted to people’s physique or attractiveness is largely biological.  Our primal ancestors had to judge mates by physical cues that suggested fertility and longevity.  Today, we don’t need those cues, but the biology remains.  What makes the human brain so great, though, is our ability to reason beyond the biological to make better decisions.  When I look for Ms. Right, I look for the girl who I think best compliments my thoughts, feelings, interests and goals.  The girl that makes me a better me, or at least makes me want to be a better me.  Attractiveness is nice, but if it’s the #1 thing you’re looking for, it just seems superficial.

Office Romance (?)

I’m sure someone out there was curious as to whether or not the girl from my office and I went out Friday night.  Unfortunately, I’m starting off this post with bad news: we didn’t.  To be fair,  I think she was exhausted.  She worked very hard throughout the week and probably needed last night to head to bed nice and early.

Around three o’clock on Friday, I noticed she had set up her laptop at a table near my desk in the office.  She was there for a good hour.  I wonder, maybe she picked that spot because she was hoping I’d drop by and say ‘hi?’  Or maybe I’m reading into signals that aren’t there.  The fact is, I didn’t drop by or say anything.  I’m not sure how to act around her during those rare moments when we intersect at the office.  Do I act professional and just say ‘hi’ and continue walking?  Do I start up a conversation?  I have no idea what’s appropriate.  I also have no idea what she wants.

The fact of the matter is, we’ve “gone out” twice, and both times it was more of an organic date that happened out of circumstance rather than someone asking someone else out.  As I pointed to in my last entry, I really like this girl.  She’s smart, passionate and gorgeous.  But both times we’ve hooked up, albeit briefly, she had been drinking.  Maybe she views those times as mistakes?

The past two Fridays, when I seemed to have missed my shot to hang out with her after work (last Friday she already had plans and this Friday she went home before I could catch her to head to bed early), I sent her a message: let me know if you want to grab a drink or a bite over the weekend.  Neither time has she followed up.  Granted, usually I prefer to try to suggest something more specific, but, again, I’m not really sure what she wants or expects — maybe she doesn’t like me that way?

Then again, she has instigated things on the rare occasion.  For example, the second time we hooked up, she leaned in for the kiss that time — the first time I had.  On Tuesday night this week, she g-chatted me out of the blue seemingly just to say hi.  Granted, she might do that to a lot of co-workers.  I don’t know.  Maybe this isn’t really an office romance at all, maybe this is two drunken hookups and my own confusion about whether or not she’s sending signals.

So how do I work this out?  I don’t think there’s a definite answer.  After I missed my chance on Friday night, I spent the night brainstorming a path forward.  I think the plan is going to be this: unless she seems to want to hang out this coming Friday after work, I’ll suggest a more specific Saturday night date — rather than my typical casual, “let me know if you want to get a bite or a drink this weekend.”  I’m thinking of saying something more along the lines of “I was going to try to cook dinner at my apartment on Saturday night, any interest in coming over as an official taster?”  I’m a decent cook and I think romance is nearly unavoidable when you cook a dinner for two.  If she doesn’t seem interested, I might just ask her point blank: “do you want me to stop trying to ask you out every weekend?” — I think I can say it playfully enough that it won’t seem frustrated or bitter, but I just don’t want to spend my time dwelling on her if she’s not interested in.

(Probably) Bad Choices

I’m a big believer in the old phrase “don’t shit where you eat,” or, for those of you who aren’t familiar with the idiom, not dating your co-workers.  At my old corporate job on the East Coast, a girl I worked with for a few weeks on a project seemed to develop feelings for me (or at least seemed to be flirting with me — though I could be mistaken) and at the time I worked very hard to rebuke her invitations to hang out outside the office as politely as I could.  That’s usually a very good move especially in a formal office environment where tact and cordiality is critical to your career path and keeping a genuine reputation.

I moved out to the West Coast and now work for a small (though growing extremely quickly) tech company where I get to wear jeans to work.  Most people in the office are also very friendly with each other, frequently hanging out outside the office.  And, as is an office tradition, we often have several rounds of drinks in the office on Friday afternoons while catching up with outside teams.  It’s actually a really fun way to work, especially when you work really long hours and weekends, it’s nice to work out with the people you also like to spend time with.

So since I’ve started, the office has grown to nearly 400 people — like I said, we’re growing from a small tech start-up to a pretty good size now.  So there are a good amount of people I don’t see very regularly.  To be fair, there are now more people in the office than there were in my high school class.  A few weeks ago, I ran in to a girl on our HR team and we ended up running out for a drink to kill time until we met up with others from our office for a co-worker’s birthday party.  I learned a lot about her background.  She’s very smart (which I like), artistic (which I like), thoughtful (which I like) and very cute (which I like, but I’m going to pretend I always look for inner beauty first, regardless of whether or not it’s true).   She has great taste in music and occasionally laughs at my terrible jokes.

We ended up spending a long time together that night.  In fact I think we probably hung out alone for a good 4-5 hours before meeting up with a crowd from the office and sticking close to each others sides throughout the rest of the night.  Of course, after hanging out for what was then 6 or 7 hours, we had a lot to drink.  And, on impulse, I kissed her.  She didn’t exactly resist, in fact she seemed to encourage it.  We were both drunk, but I’d be lying if I said I hadn’t developed something of a major crush on her throughout the night.  Moreover, I can’t deny my heart wasn’t absolutely racing the entire time I spent with her after getting to know her.

I walked her home and we kissed several more times on the way to her place.  To be honest, I think partially (or perhaps entirely) due to her drunken state I think we could have gone “all the way” that night.  But I was sober enough to push back a little bit.  I don’t like having one night stands, especially when a girl is drunk and possibly making a decision she wouldn’t want to make when she was sober.  I’d rather “earn” that with a girl through trust and hopefully mutual feelings.  I walked her to her apartment, said goodnight and literally ran home out of excitement.

That was actually three weeks ago.  Two weeks ago, we hung out again a little bit but we were both exhausted.  Though we did end the night with a kiss again.  Last week she was busy.  Now it’s Friday and I’m not sure if I should ask her out after work again or not.  If this wasn’t a girl from my office, I’d schedule something on Wednesday.  But because I work with her, I have no idea how to handle it.  Perhaps luckily perhaps not, I rarely see her at work — she’s in HR and I’m in marketing, so there’s rarely a reason for us to cross paths.

I get the feeling that this is still a bad idea.  But I really like her.  Anyone ever had a positive experience dating in the office?  A recent study showed that 31% of office romances develop into marriages, so it can’t always be bad, right?

Needless to say I’ll be aggressively cleaning my apartment this morning.  Just in case.