The Time I Wasn’t Actually Dumped

In previous posts, I’ve been mentioned the girl from my office who I like a lot.  However, as time has passed, I’ve found it more difficult to try pursue anything with her.  She rarely seems to express interest in me, though she is the one who kissed me on our second date.  I tried to decipher her intentions of sitting near my desk at work one time, a handful of late night IMs and perhaps purposefully walking by my desk at the of the day on a Friday.  All of those events may have been signals that we should continue things or they may have just been me seeing signs that weren’t there.  So, because I’m uncomfortable trying to express any type of romantic interest while physically in the office, I’m pretty much placing her on the back burner.  It’s been three weeks since we went out for a second time and she’s showed no interest in spending time with me, despite a handful of my own subtle attempts to ask her out (“Let me know if you’re at all interested in getting a bite this weekend” “Will do!”).

But then something serendipitous happened.

At the beginning of February, before I started this blog, I thought I was dumped by a girl, a Grad Student, after two dates.  She had sent me a text saying she wanted to cancel our third date.  She “wasn’t feeling it” and said she had to settle some personal issues — I took that as an “it’s not you, it’s me” break up line.  I liked her a lot, she intrigued me, but I wasn’t completely heartbroken — things are always easier if they reject you early on.  I ended up trying hard to look on the bright side and moved on fairly quickly despite two nights of mild depression about it.

Fast forward five weeks.  I get a text message from Grad School Girl on a Saturday night.

Grad School Girl: “Hey! What are you up to tomorrow?”

Me: “Hi! Actually a friend is in town from the East Coast and we’re doing brunch tomorrow, but I should be free after 1 pm.  What’s up?”

Grad School Girl: “Gotcha! I wanted to see if you were interested in farmers-marketing in the AM but perhaps another time. (I’ve resolved [some of the personal things I was going through] and would love to hang out if you’re still down 🙂 )”

Me: “I’ll have to take a rain check” … “But let’s hangout sometime soon”

Grad School Girl: “Sounds good.”

Okay, so for the five weeks preceding this conversation, I was very confident this girl had dumped me and moved on.  I was now pursuing Office Girl and had come to terms that she wasn’t interested in me.  But, to be honest, I was still really attracted to Grad Student Girl.  She was smart, extremely talented, witty and gorgeous.  We actually texted a few more times that night, just catching up a little bit.  But soon after, I got sucked into work (and was in the process of giving up on Office Girl) and didn’t actually officially follow up on meeting up with Grad School Girl — I had already spent weeks training myself not to think about her.  So three weeks later she sends me another text while I’m literally on my way to the airport asking if I was free that night.  I wasn’t, but I promised I would let her know when I got back to the west coast I would reach out to her.

So early last week I returned to San Francisco and sent her a text setting up dinner.  She’s vegan, so I threw out a vegan restaurant and we agreed to meet there.  Dinner was a little awkward, since it was kind of like a first date but also kind of like a third date.  We had gone on two dates at the end of January / beginning of February over the course of 6 days and then hadn’t spoken for over a month.  After a bit, we started developing something of a report, catching up on the issues she had worked through as well as some of my own personal chaos.  We wrapped up dinner pretty quickly, which I surreptitiously paid for while she was in the bathroom (she wanted to split it, which I like, but sometimes I like to pay — especially since she’s a student and I have a full time job).

She quickly suggested drinks and we wandered around the neighborhood a bit looking for a bar we might like.  After accidentally going into a lesbian bar, we found a crowded Irish pub where I got a beer and she had a whiskey.  We got into more deeper topics while we were there and, I think, for the first time had a slightly deeper connection than our previous conversations, which I felt good about.  Two drinks later, she suggests we go back to her apartment and have one more drink and who am I to say ‘no’ to a question like that?

We actually end up going back to my place where I open a bottle of wine.  We spend the next 2-3 hours taking turns playing my guitar — she has an incredible voice and writes beautiful songs, compared to my amateur self taught mimicry of Mumford and Sons.  I don’t remember exactly how she made the move, but at some point she ended up sitting very close to me and she leaned in and kissed me.  I had spent the past hour trying to figure out how I could find a way to kiss her, but I suppose she was feeling more aggressive than me.  We kissed several more times.  I considered pushing things forward, but decided not to considering how much she had to drink.  I didn’t want this to become a drunken mistake, I wanted it to be a beautiful night.  It was at least 2 am and she said that she should probably head out soon and I subtly responded implying that she should spend the night.  We kept getting distracted by conversation and by 3 am, we’re both exhausted and literally falling asleep.  As she doses off, I tell her we should just go to bed.  We curled up in my bed (clothed) and both fell into a drunken sleep.

At 8 am, I got up to get us glasses of water and when I got back to the bedroom she was getting ready to leave.  Had she been interested in staying I might have offered to make breakfast.  But she needed contact solution and things to do, so she got her things together and headed for the door.  I kissed her goodbye and she was gone.


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.

Act of Desparation? Men on Dattch

Working for a tech company, it’s difficult to go a few hours without perusing the tech press.  I came across an article while on my way home from work today on The Next Web.  The article covers the beta release of a new data app called “Dattch” that’s oriented towards lesbian dating.  This is an interesting niche as there aren’t many dating websites or apps devoted strictly towards lesbian dating.  Granted, there are some popular gay hookup apps, but none oriented towards relationships.  Currently the app is beta testing in the UK, but has intentions to roll out internationally sometime soon.

About halfway through the article, I couldn’t help but notice passage:

The idea of men making fake profiles to browse a lesbian site might sound spurious but Exton has been surprised at the rate and extent to which this happens. “Daily, we have about five guys registering for an invite and it’s unsubstantiated but the emails have a guy’s name on them. We’ve seen fake Facebook accounts set up to try and get invites. You’ll see they set up an account yesterday, have no friends but they like Dattch and something like ‘Lesbian and bi girlies of London’. It’s amazing. The fact that people will go to that extent to try and check out gay women or convert them or meet up with them.”

Now, I’ve been more or less single for about a year and a half.  And, like many (most?) men, I do find girl-on-girl erotica to be one hell of a turn on.  But, seriously?  What’s the game plan behind this?  Sign up for a lesbian dating site, set up a date and then reveal yourself to be a dude once you meet in person?  I’m sure this will go over real well.  Surely, she’ll realize that she’s no longer gay and invite you to a massive lesbian orgy that you’ve always fantasized about.  I can only think of maybe four or five gay female friends that I have and to be honest, the fact that their gay has really taken any potential sexual tension out of our interactions.  Do some guys think that being on a lesbian dating website will lead to something?  I know there are still people in the US who think that being gay is a choice — and I’m not looking to start a debate here — but there’s pretty much zero chance you’re about to “convert” a gay woman to go out with you via a lesbian dating app.  I don’t really get it.

[via The Next Web]

Apartment Preparedness

I’m not one to sleep with a girl on the first date.  I have a lot of friends who assure me that the third date is nearly a guarantee, but I don’t really subscribe to that theory either.  I like to let that part of a relationship evolve organically.  But, that doesn’t mean I don’t like to be prepared just in case.

I keep my apartment fairly clean generally.  I vacuum at least once a week, my bathroom is pretty spotless, and my furniture is all in pretty good shape.  But there are things I generally don’t keep 100% visitor-ready.  I rarely make my bed, for example.  Often, I’ll throw a sweater or two on a chair in my bedroom when I decide I don’t need that many layers and not re-fold them until a few days later.  I’ve been teaching myself guitar (gradually) and sometimes I leave it lying on a sofa in my living room.  So, the apartment isn’t spotless.

But I must admit, Thursday night and Friday morning, I start cleaning — just in case — and carefully make my bed.  And, to be honest, it’s not in case a girl wants to spend the night, it’s really just in case she wants to come up for a glass of wine or to hear my awful guitar playing.  I’ve never pressured a girl into anything and I’m quite proud of that.  In fact, I’ve at least twice had to turn a girl down after she got drunk and seemed to want to go uhhhh all the way that night.  In both cases, I didn’t want to ruin a potential relationship by having a one night stand with a girl who seemed really great.

I also keep my apartment stocked, just in case.  Plenty of extra toilet paper, extra new toothbrushes and mouthwash, plenty of clean towels, a collection of hotel soaps and shampoos, tissues, etc.  This isn’t really in preparation for the one night stand, rather it’s in preparation for date number x where a girl does decide to spend the night.  I think it’s a nice courtesy to have enough hygienic products so if they do spend the night, they at least feel comfortable.  Honestly, I think a lot of these things have been more helpful with friends spending the night on my couch considering I’ve only had a grand total of four girls who weren’t old friends ever spend the night at my place.

Is this a common practice?  My bet is that a lot of guys do something similar.  But, I do have female friends who have horror stories of waking up at some guy’s place where he doesn’t even have a clean toilet seat.

A bonus I’ve been considering lately is keeping around more cooking supplies — I think it could be fun to make breakfast with a girl the next morning.  Not something I’ve ever tried early on in a relationship, but it seems like a good way to transition from the early morning pillow talk.

The Mobile Digital Self

On a date a few weeks ago I found myself really connecting to the girl I was out with.  We were at a bar in Nob Hill and were texting some mutual friends.  After a while, she decided to take the liberty of using my iPhone to text on behalf of both of us.  As she explored my phone, she started going through my contact list and noticed that while almost all of my contacts are people’s full names, there are a handful of one-named contacts.  In every case it’s usually a girl’s name: Courtney, Danielle, Emily, Jen, Jill, etc…  She jumps to the (correct) conclusion that these are all phone numbers of girls I’ve been out with — or at least, as she guessed, girls who had given me their number.  I laughed it off and hoped that she was kidding.

Luckily, she didn’t get too deep into the folders of apps on my phone or she would’ve found my OKCupid app (which has 8 unchecked notifications on it).  We didn’t meet on OKCupid, we met organically, so I have no idea what her attitude towards the site is.  Most people are okay with it, a handful are not.  At the same time, I didn’t want her to get the impression that I’m some sort of guy looking for a one night stand or a “player.”  I’m not.  In fact, only once in my life have I ever dated more than one girl within the same time period (I’ll get to that in a later post) and I felt overwhelmed and kind of guilty about it — though I wasn’t exclusive with either girl.  The girl I was out with seemed like a great person and the last thing I wanted to do was have her think I’m looking for a one night stand.

So that begs the question: what steps, if any, should you take to make sure your smart phone is date-safe.  By that, I mean, do you want to have all the text conversations from your old girlfriend deleted?  Should you delete or at least try to hide all your dating apps so they can’t see what you’ve been up to?  How long should you wait after you stop seeing someone to remove their contact info from your phone?

I don’t think there’s a right or wrong answer here.  In fact, it’s probably pretty rare a girl is going to go through your phone on the first date.  But it’s probably something that’s worth being prepared for.

OKcupid Skipped Questions: Hairy Issues

Do Women Have an Obligation to Shave Their Legs?

Do Women Have an Obligation to Shave Their Legs?

There are tons of interesting and sometimes thought provoking questions on OKCupid, everyone’s favorite free dating website.  But then there are questions that are difficult to answer.  Here’s a recent example that’s been frustrating me:

Do you think women have an obligation to keep their legs shaved?

My direct answer to this is: no, of course not.  However, at the same time, I would prefer a woman who shaves her legs.  By selecting no, it’s more likely that I’m going to matched with a girl with hairy legs, which is a big turn off for me (and probably a lot of other men).

Just to clarify my position on women and shaved legs, let’s look at the issue here.  Shaving any body part is a hygiene choice and therefore personal.  Women have no obligation to shave their legs, armpits, chest, arms, whatever any more than a man does to shave his face or trim his sideburns.  Do I find it more attractive when a woman has shaved legs?  Yes.  Do I feel like a woman is doing something inherently wrong by not shaving her legs?  No.  Good for her, it’s her choice.  Further, I have absolutely no right to tell a girl that she has to shave body parts or wear makeup or confirm or do anything else that I think makes her look pretty.  In return, if I choose to grow a beard — though my beard doesn’t exactly grow in the way I’d like it to — I don’t think a woman has the right to tell me I’m obligated to shave (the exception to this, of course, is if I’m offered a spot on the Yankees).  I’m also not obligated to brush my teeth or shower, though I imagine most women would prefer this.  Similarly, most men probably prefer a woman with shaven legs.  Though, this whole shaven legs thing is actually a style that’s less than 100 years old.

But, again, here’s the problem with this question: I don’t want to date a girl who doesn’t shave her legs.  I once actually dated a girl who didn’t shave above the kneecap and it was a huge turnoff for me.  I don’t know why, I can’t explain it — for men prior to 1920, this was normal — but I didn’t like it.  So part of me is inclined to answer “yes” just to be sure that every girl I’m matched with is shaving her legs.  Of course, that also means that every girl that I’m matched with might also think women are obligated to stay home and take care of their families, or think that Saudi Arabia is on to something when they forbid women from driving cars.  The small subset of women who have their gender philosophies dwelling in the past like that are also turn-offs for me.

So how do I answer this question?  I don’t.  I skip it.  I could answer it privately but then most people will assume I answer that women are obligated to shave their legs — and I don’t want them to think that!

It’s a vicious cycle.