The Dating Continues…

I hate to leave things hanging so now that it is almost the end of September, I should tell you how my August dating challenge ended up. The goal was to go on one date a week and I managed to almost do that (if going out with the same guy in two different weeks counts and I say it does) before things with the Sommolier came to an end in late August. Technically, I was one week short but I did go out with one more guy (“the artist”) in early September. As a recovering perfectionist, I say this counts as success.

I won’t say too much about “the artist” at this point except that he is a very interesting (and cute) guy who has managed to get to a fourth date, which does not happen often.

Earlier this week, I reflected back on my dating life and realized that I have been on dates with more guys in 2013 than in the 5 years before 2013. And there were no long-term relationships in those 5 years, just not a lot of dates.

So when people ask me why such a fabulous and attractive (and clearly modest) woman is still single at my age, I can definitely say that one big reason is that I didn’t really date.

I may have mentioned (repeatedly) that I don’t like dating. Going out with 8 different guys in 2013 has not been all fun and games. Mostly, it is a huge pain in the ass. Finding a night that works, picking a place, making conversation, figuring out how to end the date, deciding whether or not you want to have another date, getting your feelings hurt, hurting other people’s feelings. Fun, fun, fun.

I’m not sure if it’s getting easier the more I do it, or it’s just as hard, but I keep doing it anyway. In the past, one annoying online date would send me back into hibernation for months or years, and I have stayed in more than one bad relationship just because I didn’t want to deal with finding someone else.

This year, I have managed to just keep getting back out there. I am no longer avoiding it, I am pushing through it. It has been a pain in the ass, but I have also met some interesting people, had some stimulating conversations, learned more about myself, shared some intimate moments, received some hilarious text messages, and opened myself up more.  The yin and the yang. You can’t have the good without the bad, right?

The dating will continue. The challenges of the first date are not the same as the challenges of the fourth date. The stakes get bigger, things get more complicated, more feelings are involved, things get more confusing. I do look forward to the day when the benefits outweigh all of this hard emotional work (and logistical scheduling!) But I also realize that the emotional hard work is never really done, not if you want to live a rich, full life with human connection, which I do (with some TV mixed in, of course!)

The Sommelier

The third date of my August dating challenge was with “the sommelier”. “The sommelier” wrote to me about a month ago on OK Cupid and I thought about writing him back, but decided not to. There was something about him that I liked (he is cute) but he is very  young and I didn’t think we would have anything in common. OK Cupid specifically said “Y’all have issues” which they put right on the screen if you are a low match (The sommelier and I are a 61% match – not great.)

Earlier this week, I met a friend for dinner at a restaurant near my office and there he was, “the sommelier”, right behind the bar. I recognized him immediately (it felt like a celebrity sighting.) I checked him out during dinner (he even stopped by our table to ask if we wanted more wine at one point,),but I was too shy to say anything. How do you say to someone “Hey, are you the guy who emailed me on OK Cupid last month?”. I did still think he was cute.

I emailed him when I got home to confirm that it was him (it was.) He was quite happy to hear from me and we decided the universe was telling us we should go out. Lucky for me, I found August date #3!!! “The sommelier” was SO excited to meet me that he proposed stopping by my office to say hello on his way to work so we could meet in person sooner than later (our schedules are not easy to coordinate). This was a random meet and greet idea that would never have occurred to me, but why not? We chatted outside my office for 15 minutes and there was chemistry. He seemed very young, but sweet, and still cute.

I have been down this much younger man path MANY times before. I know the dynamic, and it never ends well, but a fun potential summer fling that lands right in your lap is hard to resist.

Unfortunately, what I learned on my second date with “the sommelier”, is that I might have outgrown the much younger man thing and I am not sure flings are my thing. This particular younger man seems very young. He is VERY in to me, which is flattering, but it is not based on anything beyond attraction. Apparently attraction without emotional connection (or anything in common) is not really that fun for me. I am still pondering whether there is any fun to be had here and I don’t want to hurt the young, sweet, sommelier. (I have not, by the way, learned anything about wine from him yet except that I what I drank at his restaurant was apparently not good wine.)

Week #4 of the August dating challenge is upon me. What to do? What to do?

The August Dating Challenge

In late July, I challenged myself to go on one date a week in the month of August. I didn’t think I would have enough options to go on that many dates, but I started on July 31st (I decided that counts) and have miraculously been on one date a week since. I have had no luck with the OK Cupid emails I am sending, but three guys emailed me that were not so bad, so I gave them a whirl. They were all very different.

We start with British Johnny. British Johnny was 6 years older than me and sold himself as talking like the gecko in the insurance commercials (I like that gecko). He seemed like an interesting guy, but my gut told me he was to formal, serious, and geeky for me. In an attempt to determine whether I am ruling people out for the right reasons, I decided to go on the date.

The date confirmed that I would have been correct to rule out British Johnny. Nice guy, smart, and has done lots of interesting things (for example he just wrote a book on esoteric wisdom), but not a good match for me. He was visibly despondent when I told him there would be no second drink. I was surprised to learn at the end of the date that in his first week back online after many years, he had 5 dates booked from the 7 emails he sent. He also mentioned during the date that he met his first wife on his first online date ever. Go British Johnny! I am sure he is doing just fine.

The next week, I went out with “suburban Jewish guy”. I don’t usually go out with guys from the suburbs but I liked his profile and we had a bit of a banter going via email so I decided to be open to it. This date was very interesting. We had intellectual compatibility and a much deeper level of conversation than I have on most dates.

During a conversation about expectations and being open, “suburban Jewish guy” told me that I seemed very shut down at the beginning of our date and that he liked me much more after my second glass of wine. (I am definitely more fun after two glasses of wine. Who isn’t?) I explained that I was very shut down for two reasons (1) I have opened myself up twice in the past year and been hurt pretty badly (2) I don’t like hurting other people and I don’t want to seem interested and lead someone on unless I am sure I am interested. (A third reason, that I did not mention, was that he texted me from his car as he drove by looking for a parking spot to tell me he thought I looked cute. This was a bit much, so I was preparing for the worst.)

He explained that me being shut down makes the other person put up their guard and makes them not interested in me. He also theorized that I am so busy keeping my guard up, that I am not really open to seeing what may be interesting about the other person. This was all true and made me realize that if I am going to do this dating thing, I have to be more open. It was actually a very emotional conversation for me. It felt a bit like a therapy session.

Although I was not really attracted to “suburban jewish guy”, I appreciated the intellectual compatibility and his perception and self awareness so I agreed to walk with him a bit after the date. When we got to the agreed location where we would part, he asked if I wanted a second date. I responded with “yes…I think so” (this was the “not so attracted to him” and “still pondering this open thing” part of me answering). He then leaned in for a kiss which I was not feeling at all.

In the spirit of being open, I did send a follow up email the next day saying I was interested in a second date and hoped my ambivalent response did not put him off. There was some text messaging (which was actually a bit weird and made me even less interested), but I think ultimately there was ambivalence on both slides and it kind of died off.

Then I got distracted by the sommelier which turned in to date #3. I will tell you about him tomorrow…

Match vs OK Cupid

I decided a couple of weeks ago that I should cast a wider net and get myself set up on another dating site. The only sites I have heard anyone talk about lately are OK Cupid and Match so decided to add Match back to my portfolio of dating sites.  (I have been off Match for over year.)

Within an hour, I regretted this decision. Unfortunately, it was after I forked over $150 for 6 months.

Now that I have experienced OK Cupid, I definitely prefer it over Match, and here are the many reasons why.

1. The user interface on Match is horrible. People’s pictures show up squished in the search. The front page is busy and distracting and I have to look at advertisements even though I PAID for my membership.

I pulled some screen shots so you can compare the two.  Not sure if you can fully get the gist with these, but you can click on them to see the experience full size.  Match is just an eye sore.

2. The profile layout on Match is distracting so you are more focused on the section headers than the actual content. There are the ugly yellow highlights that show you the things you have in common like “coffee/conversation” and “travel”. There are cheesy icons displayed when you look at someones profile like a sneaker that says next to it “you both like running”. Woo hoo!

Here are some profile samples (hopefully they won’t sue me!).  See how OK Cupid is just much cooler?

3. Match lists whether you have ever been married before right at the top of the profile. (On OK Cupid it is one of a thousand questions you can answer but you don’t have to) When I first joined OK Cupid, I wished that information was right up front, because I would be very wary of a 44-year old that has not been married. But now that I am a 44-year-old woman who has never been married, I realize this does not play to my advantage.

5. Match requires an email subject when you send a message.  I never gave this much thought before, but I love how on OK Cupid, I can just write a quick note and not try to come up with something catchy in an email subject. “Hey” or “Hi there” is annoying, but coming up with something witty in the subject AND in the email is just too hard.  I have tried “Pretend I put something witty here”. I didn’t get a reply.

6. When you make an update to your Match profile, the text and the photos have to be approved before they show up (each separately.) It took almost 12 hours before my photos appeared on my profile.

7. You can hide your profile which means you can click on profiles without people seeing you clicked on them, but if you change your profile, it seems to automatically become unhidden when any part of it is approved. I was not aware of this and went on a favoriting rampage (OK only 4 guys I found suitable) while I was waiting for approval and they all saw that I favorited them and looked at my profile before all of my super cute photos were posted. I was pissed.  UPDATE: I have since learned that you can’t really look at people without them knowing because when you un-hide yourself, you become visible in people’s visitor list, always. This had nothing to do with the profile un-hiding itself.  This feature change is not cool.

8. I think there are a lot more people on Match, which was what I was looking for in “casting a wider net,” but that also means there are more not-so-great profiles to wade through.  It is hard to stay positive while wading through the “not so great” profiles. Ugh.

9. There is one plus to Match over  OK Cupid.  Match emails you the whole email message someone sends you. OK Cupid only sends the first sentence or so, so you HAVE to log in to OK Cupid to read the message. This is easy since you can log in on your phone from anywhere, but then the sender knows for sure you have read it and not emailed them back.

Match has definitely made me appreciate OK Cupid more. Here are some things I realized that I really like about OK Cupid.

  • The free-form questions on OK Cupid are more interesting so they make it easier to express who you are beyond just one paragraph.
  • OK Cupid has hundreds of random multiple-choice questions you can answer and see people’s responses and whether you match. These tell you basic things about people that are not in their profile (it looks like they are adding some of those on Match). They also drive a match % which displays for every person on the site is actually, kind of helpful.
  • OK Cupid shows you whether someone will “reply often” or “very selectively” so you have an idea of whether this person blows everyone off, or just you.
  • All of the artists, and teachers, and creative types on OK Cupid (because it is free) make it much more interesting and it feels cooler. Match seems to have a lot more average guys from the suburbs to wade through.
  • The site is free, but I can pay an extra $15/month to view profiles invisibly. Love this feature and I don’t have to remember to hide my profile when I want to browse (that is such a pain in the but!)

Overall, Match just feels really old school compared to OK Cupid. OK Cupid is a really stupid site name, but despite that, it is definitely a better experience. As good as an online dating experience can be, I guess. Since the same company owns them both, I guess they make money either way. Extra money from me!

Another Perfectly Nice Guy

I just returned from a date with “software guy”.  Another perfectly nice guy. We chatted for two hours about various things. Within the first 5 seconds I was fairly sure there was no attraction, but there was a glimmer of possibility, so I was able to keep an open mind about it and carry on. (Wine is so super helpful in these scenarios.)

There really isn’t anything all that interesting to write about this date. I knew almost nothing about this person before we met. He seemed more two dimensional in person than his profile made him out to be. It is hard to explain, but he was more “flat” in person.

He remembered almost nothing that I told him about myself in the emails we exchanged. I didn’t tell him much! That was a turn off.

He went on slightly too long about his last relationship and why it ended.  For a first date, it was a bit odd, like he was still struggling with it, perhaps. I can certainly relate to the struggle, but not good first date conversation, especially not in this depth.

In the middle of the date I realized that his mannerisms reminded me of someone I knew but I couldn’t quite place it. I finally realized it was this guy that I worked with many years ago that we had nicknamed “the Stay Puft Marshmallow man.” We gave “Stay Puft” his nick name because he was puffy in stature, never stopped talking, was full of hot air,  and was kind of annoying. In all fairness, “Software guy” had none of these qualities but his mannerisms did remind me of “Stay Puft”. It was pretty unlikely that romantic feelings were going to set in after I realized this.

Overall, there was just no spark. Now that I think of it, he was missing both the required dry sense of humor and the required sex appeal.

The good news is, this date was not super painful, we parted with a “have a nice holiday weekend” (so there might have been mutual disinterest.. yes!!!!) and, the best part was that he gave me his perfect margarita recipe! This bodes well for July 4th signature cocktails.

Addendum: I just noticed that “software guy” checked OK Cupid while I was in the bathroom towards the end of our date. Nice move “software guy.” Confirmed mutual disinterest.

Let the Games Begin

I finally have a date lined up with “software guy” tomorrow (that I will be sure to tell you all about), but I decided that I have to increase my throughput of dates if I am ever going to get to the end of dating. Single threading is not going to cut it. This is a numbers game and one might theorize that I am still single because my number of attempts is low.

In the spirit of all of that, I picked a guy who had clicked on my profile a couple of times and sent him a message this weekend. He replied (because clearly my new profile is like magic!) but as soon as he replied, I had a weird feeling about him. Maybe because his name was Tony. This makes absolutely no sense, but apparently, I am completely prejudice about the name Tony. It reminds me of mobsters. I racked my brain for someone cool named Tony. The only person I could come up with was Tony Goldwyn who plays the president on Scandal. (The internet has also just reminded me of Tony Stark, aka. Ironman.)

So I had a bad feeling but I had sense enough to realize I could not just blow this guy off because his name was Tony. Within two more quick emails I learned that he stopped in bars to cool off while he was running errands on Saturday and that he has an aol email address.  These were not good data points. His profile was borderline heavy drinker and the bar thing swung him more in that direction and aol is even more old school than my yahoo account. (One of my friends tried to convince me it was retro, but I wasn’t buying it.)

Again, I told myself I should press on. I am on vacation this week and there is no reason I should not spend one hour to see if my gut was right on this guy, so I agreed to meet him for a drink. Although he sent me his number and email address, I was not comfortable sending mine so I just ignored it and continued to chat on OK Cupid.

After we settled on date and time and location he pressed me again for my contact info.  I gave him some line about not giving out my contact info until after the first date because that “seemed prudent in this crazy city of ours (with a smiley face)” I usually do give out my contact info, but there is really no reason to do this since you can get and send OK Cupid emails on your phone and there really are a lot of crazy people out there. I would prefer that people that I don’t want to date, not have my phone number and email address.

While I was lamenting the fact that I ever contacted this guy and debating whether I could make something up to get out of it, a miracle happened. I got this email in response to me not providing my contact information.

“I will have to cancel then. Good Luck”

At first, I thought he might be kidding. But if it was a joke, it was a bad joke. It did occurred to me that he could think that I am hiding something or some weird neurotic person. Either way, I had my out! I responded.

“No problem. Good luck to you too.”

Problem solved! Isn’t online dating fun?

What’s Up With Tinder?

The other day, I was reading one of the many blogs written by women about their online dating adventures. (Are there any MEN that write about this ridiculousness because I would really love to hear the perspective from the other side. If anyone knows of a blog like this, do tell.) Anyway, Stupid Cupid mentioned that she was getting endless hours of entertainment on something called Tinder. I immediately Googled it and found this article in the Huffington Post that called it not a dating app but more like a “beauty contest with messaging.” I was curious, of course,  and decided to check it out.

Tinder is a mobile app that presents pictures of people to you that you either “like” or “nope” by hitting a button or swiping them off the screen. All you know about this person is their age, how far away they are from you, the last time they were active, and maybe a sentence or two if they enter some words. Oh, and you log in with Facebook so you will also see if you have mutual friends or interests. You can only message someone if you have both “liked” each other. So basically, the only thing you can get from this app is to find out if the people who you think have hot pictures think your pictures are hot. Sounds like a great way to find love. Not so much. But not totally un-fun.

I downloaded the app and mostly “noped” but also “liked” some dudes. One guy looked pretty familiar and I was fairly certain he and I had exchanged a couple of messages on OK Cupid one night before he drifted off and got distracted by someone else. His pictures were different, but I was pretty sure it was the same guy. I decided to like him because I still thought he was cute (although probably not dating material) and decided to see what would happen.

Within 12 hours, the guy from OK Cupid liked me back. Or maybe he liked me before I liked him? Anyway, we matched. I refuse to actually message him because he blew me off last time. He has not messaged me. He probably figured it out. Weird dude.  That is my only actual match so far. I did just like one cute guy who is friends with a friend of mine from my very first job. That is interesting to know…

I have to say, it is a little bit addicting to flip through pics and “like” or “nope” them. This guy Bjorn is pretty cute. He is also really good at taking self photos (he has five of them). Self photos are usually a big no-no because they turn out creepy, but this guy is a professional at it. This may entertain me until I finally have my date with “software guy” this week..

Getting Back on the Horse

I went on a date last week. It was my first date since the Teacher. Since I am dating again, you can probably conclude that the Teacher is no more. It was awesome for a while, and then things got complicated. The good news is…you get to read about my online dating adventures again!

I turned my OK Cupid profile back on a few weeks ago when I decided it was time to “get back on the horse.” I emailed a couple of guys. My new and improved profile seems to still be yielding better results because I got a quick response from this guy who seemed very normal and cute (and he actually was very normal and cute.) His profile said he was a planner. I, of course, was digging that. We quickly and efficiently made a plan. He did not disappear after a couple of emails. He communicated with me the completely appropriate amount and seemed genuinely excited (at an appropriate level) to meet me. I was somewhere between indifferent and nervous (this being my first time back on the horse in a while.)

We met for a drink near where we both (serendipitously) work. I was pretty sure within the first 2 minutes that there was not a connection between “the planner” and I, but I tried to stay open. Such a nice guy, and attractive, just no connection. We made conversation, but there were many awkward pauses. It got a little bit easier after I finished my first glass of wine. Just as I was finishing that up, he told me this was his FIRST online dating experience ever and almost his first date since his divorce. This confession put a lot of pressure on me to show him the ropes and give him a good experience. He even asked me to let him know if he was doing anything wrong (sweet guy).

After our first drink, he asked me if I wanted to grab dinner. I was trying so hard to have an open mind and not disappoint him on his first online date ever (and I had just finished a full glass of wine) so I said yes. I also wanted to postpone that moment when you reveal to someone, in a nice way, that you are just not that in to them.  I hate that moment. I might hate it even more than the moment when someone reveals to you, in a nice way, that THEY are just not into YOU. I guess they both suck. Given my martyr personality, it is often easier for me to take this hit myself. These moments make dating hard for a super nice person like myself.

Anyway, we had dinner and it was pleasant enough. (My burger was amazing.) We had some things in common but he was missing two very important things: a dry/sarcastic sense of humor and sex appeal.  These are deal breakers for me.  People without these two things will not work for me. Those might be the only two things that I need.  OK, maybe I need more than that, but they are really important.

At one point during dinner I started to try to explain why I hate dating. I can’t even remember how that came up (somewhere in the middle of my second drink.) The words ” I just don’t really like meeting new people” came out of my mouth (What was I saying?? Although this is kind of true.) I think I was trying to explain that I don’t have any interest in just finding someone to do stuff with. If I don’t genuinely like hanging out with you, I would rather be by myself.  And I was thinking that he fell in this category but I was still not ready to reveal that because we were mid-dinner and I wanted to finish my fries. That line of discussion ended with an awkward pause.

I also remember saying “This isn’t too painful, right?” To that, he said something like “painful is not what I was thinking at all”. Another awkward moment. I was not my best self on this date. (Although he did seem pretty impressed that a person who does juice cleanses would also eat a burger and fries. That does make me pretty awesome.)

The date finally ended with him finding me a cab in the rain (such a nice guy), then trying to kiss my on the lips while I quickly turned to go for the cheek, and him saying “we should talk soon” and me saying “yeah, sure” and avoiding eye contact. (The final awkward moment of the night.)

I guess he got the hint because I did not hear from him again, but I wanted to write to him and say “You did a perfect job on your first online date ever.  You did everything right and you are a great catch for most other women.”  Of course it is totally possible that he was not that in to me either. Reflecting on my lack of interest in asking him questions and the stupid things that did come out of my mouth, this is quite likely.

I officially saddled up the horse and took her out for a ride. I am currently in the process of scheduling a date with “software guy” who actually wrote to me. The horse is out of the stable.

I am going to try to become a person who likes meeting new people. I like people!  People like me! I know there are many interesting people out there besides my fabulous friends and family and the guys I used to date and keep accumulating as Facebook friends. I live in the greatest city in the world, full of fabulous people.  I will find them and enjoy every minute of it! Here I go…

Something Changed…

A couple of weeks ago I told you that I was headed to Hawaii, I had taken my revised online profile out for a spin, I was chatting on OK Cupid with a teacher, and I was planning to have a bevy of dates when I got back from my trip.

Hawaii was fabulous. My sister and I relaxed in the sun (more often in the shade) and shared many beautiful sunsets together that even I (a horrible photographer) managed to capture in a photograph.

While I was enjoying the view with my sister, I continued to chat with the teacher and it became very clear that he is pretty awesome. The OK cupid chatting turned into a lot of e-mails which progressed to phone calls and text messages, and two dates….so far. The first date was the best first date I’ve ever had.

You might be interested to know that OK Cupid scored us a 95% match. He thinks we might be closer to 97.8%. Even though he is not a math guy, I think he got this one right.

Did I connect with the teacher because my profile got an overhaul or was it just online serendipity?  I do know that I would not have bumped into him at the JCC Shabbat dinner (even though he is Jewish.)

Suffice it to say, that if things continue this way, I am not planning on writing about online dating again any time soon. (Please note my glass half full optimism.)

Disappearing Dude #2

I revealed my new profile to the OK Cupid world last week, but I was still not happy with it. I perused some other profiles that I liked and used them to inspire some changes. I think my new version shows a bit more style in the writing while still keeping it short and light? It got the thumbs up from two of my biggest fans! Because I got you all involved, I think you should know what I ended up with. There is more to the profile that says more about me. Think of this as just the intro..

Last week’s “after” Self Summary that I still didn’t love:  I’ve been a New Yorker since college and I can’t imagine living anywhere else. Although I am a city girl at heart, I do like to explore far-away places with friends or that special someone. Last year I traveled to Bali (amazing!) and Istanbul is on the top of my list for 2013. I own my own place with easy access to runs on the river and my favorite spots in the East Village. I am a bit of an entertainment junky so I challenge you to keep up with my knowledge of pop culture. My friends and family are a big part of my life, especially my adorable nieces. If the right man were to find his way into my heart, I hope he would be up for and princess birthday party or family visits in the big city from time to time…

New version with more personality: Caring, curious, and down to earth. I’m a long-time New Yorker who prefers downtown to uptown and loves people watching, laughing, and learning new things. I am a bit of an entertainment junky so I challenge you to keep up with my knowledge of pop culture. A former jet-setting consultant, I now use my passport for fun adventures to far-away places like Bali and Marrakesh. Yoga, runs on the east river, and my morning coffee keep me balanced and sane on my daily quest to make the most out of life and keep it real. 

So how did it go?

I emailed two guys. One guy was, according to his profile, THE perfect guy for me. He works in technology, recent widow, volunteered at an orphanage as part of a year off he took traveling around the world, runs marathons AND does Pilates, and has cute pics that showed personality. Except for the fact that he likes Coldplay, he really seemed perfect. I also emailed a backup guy who seemed cool but not THE perfect guy.

The perfect guy never replied (not so perfect!)  The backup guy did reply, two days later after checking out my profile a few times. (Clearly ambivalent.) We exchanged a couple of short emails and then he asked me if I wanted to have a drink sometime.  I said “sure, what are you up to this weekend?”  No word since.  That was Wednesday morning. It’s now Saturday. He disappeared. With OK Cupid I can see how often he logs in and if he looks at my profile. He has logged in every day and has not checked my profile since. He clearly found something that seemed more interesting.  You may recall this happened to only one other guy that initially replied to me. He asked for my number and never called.

That’s the update. I guess I should send out more emails. I am fighting the longest cold in the history of the world (I hear this is going around) but I should still send some emails. The show must go on!