Dating… love… and guilt.

Last week, I wrote about having deal-breakers and standards, and the importance of staying true to yourself.  The other piece of that that I didn’t mention is that whole “guilt” thing.  Dating is full of many different emotions and guilt is most certainly one of them.  Don’t get me wrong, a little guilt is not such a bad thing.  When a guy invites me to sushi and then changes his mind and offers pizza, believe me, I want him to feel a little guilty about dashing my sushi dreams for that evening (insert violins here).  

The guilt that becomes problematic is when it forces us to settle.  I am very fortunate to know a lot of wonderful people.  Because I have such a wide circle of friends, I have watched a lot of relationships come and go.  It is, of course, so sad when people break up, especially if they are two good people who are just not meant to be.  Whenever this happens to people I know, someone always feels guilty.  I hear a lot of “she’s such a great girl…. I never meant to hurt her…. this feels so awful.”  Yes, it does.

The problem comes when they turn into these sentences: “Maybe I was wrong…. maybe she will change… I feel so bad, maybe I should give her another chance.”  A good friend of mine recently broke up with her boyfriend and felt so terrible for hurting him that she almost went back to him just so she would feel less guilty.  She knew deep in her heart it was not right but the guilt just overcame her.  What happened?  Six weeks later it ended… again… even messier this time.

I am not saying that we don’t make mistakes.  Sometimes, people really do deserve a second chance and it does end up working out.  I think though, that when someone considers giving an ex a second chance it can’t be about guilt.  Guilt is powerful but it doesn’t fix anything, or change anything, it just is… and eventually it goes away (hopefully).

I dated a guy a few years ago that I really cared for.  He was truly a good guy.  When he ended things with me, I had this strange combination of feelings– I was heartbroken, but I got it.  He knew in his heart that I was not the one for him.  It wasn’t that he didn’t care about me, or that he didn’t enjoy spending time with me, or even that he wouldn’t miss me.  It was that he didn’t feel we were meant to be for a variety of reasons that looking back, all make sense.  I share this story because I am very grateful to that man for breaking up with me (now there’s a sentence I never imagined writing).  At the time I was so sad, and I know that made him feel terrible.  But, the reality, MY reality, is that I never want to be with someone who doesn’t love me without question, 100%, and WANT to be with me.  Don’t we all deserve that?  Don’t we all deserve to be with someone who wants to be with us as much as we want to be with them?

I guess I say this to both those who feel guilty and those who are the ones who’ve been hurt… Guilt is real, and powerful, and at times consumes you.  However, it is not a healthy basis for a relationship.  It is not a reason to be with someone.  Do not forget who you are and the things you are not willing to compromise… that is not something to feel guilty about.

Now if you eat my dessert…. then you can go ahead and feel guilty enough to buy me another one.  

That seems reasonable.



So that happened… (episode 1)

Since beginning my blog I have been inundated with dating horror stories from fellow love-seekers out there.  I decided every so often I will post one of these lovely stories.  Thanks to this anonymous contributor for her story!  Please note this one is rated R due to content…

After being dumped by a guy who was still in love with his ex-girlfriend, I decided to give a try. I signed up for a 3-month membership and spent several hours crafting my profile, cropping and auto-enhancing the most flattering pictures I could find and doing my best to sound as smart, sophisticated and fun-loving as every other twenty-something in ODL (online dating land). 

Soon after “launching” my completed profile, I was ready to check out some dudes. A profile with the name “ImperviousToCold” caught my attention–a graduate student at a prestigious university, he seemed smart, interesting, and pretty cute. We messaged back and forth several times and decided to meet in person.
The first date was, for lack of a better description, slightly uncomfortable. We met for drinks at a swanky bar of his choosing, where my Marshall’s skirt and I felt very out of place. The conversation flowed fairly easily, but he was somewhat cocky and criticized my favorite author. My older, more mature self wouldn’t have even entertained the thought of a second date, but immaturity and low self-esteem clouded my judgement and I decided to give Mr. Not-So-Modest another shot.
On the second date, we met up at a more relaxed bar for drinks and a few rounds of ping-pong, which was much more my style. After several cocktails and failed attempts at appearing the least bit athletic, we ended up at his parents’ expensive and tastefully decorated apartment (they were out of the country, probably hobnobbing with royalty and bathing in foie gras). We sat down in the living room, where awkward small talk led to a makeout session of epic proportions. Now, when I say epic proportions, I mean that there was an epic amount of saliva on and around my mouth–my chin, my nose, undoubtedly my hair. So much of his saliva was where it shouldn’t have been that I was concerned he might have dry mouth. He must have gotten a hint from my aggressively closed-mouth kissing, and turned the intensity down a few notches.
Mr. Not-So-Suave led me into his bedroom, where I discovered that you’re never too young to wear pleated khaki pants above the belly button. Various articles of clothing later, our makeout session turned horizontal. As we rounded third base, the Steven Tyler mouth was back and in full effect. Desperate for air in my lungs and a blow dryer on my face, I put the brakes on our intense cuddling. Mr. Not-So-Lucky laid back on the bed next to me, and made some remark about the home run he’d just hit. Excuse me? Was there another woman in the room? Because from my very sober point of view, nothing had entered my–er–home plate. I tried to assure him that he had not scored, but he was convinced that the deed had been done. Was he a virgin? Wishful thinking? I’m not a particularly large person, so it didn’t seem to be a case of getting “lost in the folds” (if you know what I mean). I left soon thereafter, with no intention of going on a third date.
Several days later, Steven Tyler called me. After our bizarre evening, I was surprised to hear from him. He stammered his way through a very awkward post-second date breakup. Relief washed over me, and I wholeheartedly agreed that the spark just wasn’t there. He continued to stumble over his words, unsure of how to end the call. I wished him good luck and hung up the phone.
Several years later, while skimming the New York Times wedding announcements, I saw a picture of Mr. Not-So with a soon-to-be Mrs. Not-So. I’ve never felt Oh-So-Lucky.

It is really okay to have deal-breakers

I once had someone tell me that having “deal-breakers” in dating meant I was boxing myself in, being too picky.  I disagree.  The art of the “deal-breaker” is that it is just that… it includes the things that are so important to you, you are not willing to compromise.  We talk about compromise in relationships a lot, because of course, compromise is extremely important.  However, I do not believe a person should compromise their beliefs or the things they hold dear to them just to “make it work” with someone.

Where did that saying even come from? “Make it work.”  That is a terrible saying.  It might apply to a workplace relationship, or a sibling relationship…. those you really should try to “make work,” but a romantic relationship?  Don’t think so.  In my opinion, the person you spend your life with should be someone you don’t have to try so hard to “make it work” with.  Now, don’t get me wrong, I know relationships are work, but a relationship should not begin with the words “let’s make it work!”

Earlier in my life I made a huge mistake.  I fell in love with someone and in order to “make it work,” I started compromising things that made me who I am.  I tried so hard to make our relationship work that in the process, I lost myself.  It took me a long time to understand what had happened but when I was able to piece back together the parts of me that had been lost, I had a huge realization.  First, that I had no one to blame for this loss of self except me.  I am the one who let those pieces of me go, no one forced me.  And second, that as wonderful as it is to be in love, we cannot lose ourselves in love.  In the process of falling in love, it is so incredibly important to make sure we are still being true to ourselves.  

This brings me back to the idea of deal-breakers.  In the beginning stages of meeting someone and getting to know them, I believe it is okay to have those few things in the back of your mind that are SO IMPORTANT, they are parts of who you are.  It is okay to be picky.  It is okay to give yourself permission to have standards.  I mean, if you are truly looking for the person you will spend the rest of your life with, I can’t think of any other more appropriate situation in which to have standards– deal-breakers– can you?  Everyone will have different things that they consider their deal-breakers.  What I might hold dear to myself is likely to be completely different than what you hold dear.

What do you want?  Go ahead, have a few deal-breakers.

Happy Monday…




And then…. there was tinder.

So this Tinder app….. why do we do this to ourselves?

For those of you who don’t know what Tinder is, allow me to explain.  Tinder is an app you can download to your smart phone.  When you open it up, it asks you for your age and to add a few photos of yourself.  You have the option to write a sentence or two underneath your pictures but most do not.  You then go to the main screen where peoples faces start popping up. Tinder provides you pictures of others (men or women, whatever you choose) in a certain mile radius and you must decide if you are interested in them.  Swiping one way means NO.  Swiping the other way means YES.  If both you and another person swipe YES, you are able to start messaging back and forth on said app.  

Now, it’s not that I don’t see the point.  For those out there that are not looking for a relationship, Tinder is great.  I assure you that if you are looking for a quick hookup, Tinder allows you to do so without even leaving the house…well I suppose one of you would have to…  But for those of us looking for something other than a one night stand, Tinder is a colossal waste of time.  This is not an opinion, this is my experience.  I tried Tinder for about 2 weeks just to see what all the hype was about.  I swiped yes to a lot of men.  I even messaged with many of these men.  I admit, it was a little exciting every time Tinder through a little party on my phone that read “you have a new match.”   On the whole, I think I spoke to about 20 men.  Out of those men, 11 asked for naked pictures of me, three asked me to talk dirty to them, three asked how much money I made and then stopped talking to me and two asked me if I was interested in having a three-some…. I wonder if they knew each other….?  One turned out to be an okay guy, didn’t go anywhere but at least he didn’t fall into any of the categories I just mentioned.  One… in twenty.  Not terrible, but not great odds.

I do think it is funny.  How many people do you know that SWEAR it is the personality that matters the most?  I am sure I have said that at some point…”looks aren’t important, it is what’s on the inside that matters!”  Well folks, that’s bull.  If that was the truth, apps like Tinder would not have so many participants.  Don’t get me wrong, at the end of the day what is on the inside DOES matter the most.  However, if you are not attracted to the other person, it’s not going anywhere.  In my opinion, the attraction gets things going, but the heart and soul are what keep it going; both are important.

The problem with apps like Tinder and other online dating tools is that you are seeing the best of the person, not the whole person.  I know that when I made my online dating profile, I picked the absolute best pictures of me and wrote only the good things in the “about me” section.  When asked about pets, instead of putting that cats scare the crap out of me and I have never really been a dog person, I just didn’t put anything at all in that section.  Instead of admitting that although I have a job I love, my salary is less than impressive, I too left that blank.  I think it is normal to want to paint yourself in the best light possible on any of these dating sites, but unfortunately, you cannot hide the bad stuff forever– not even the bad stuff…. just the REAL stuff.  At some point, I hope I will reach a point where I put the picture up of me with no makeup and my crazy curly hair instead of the one with my perfectly overdone makeup and time consumingly- blow-dried hair.  At some point…. like in 60 years.

Until next time,


Reason 1,538 why I love online dating…

As I think many of you will agree, online dating sucks.  But the reality is, there just aren’t a lot of good ways to meet people, so a few years ago, my love/hate relationship with online dating began.  I admit, I have tried a variety of websites… probably MOST of them.  As a nice Jewish girl…. well… a Jewish girl… I decided to start with Jdate.  For those of you who don’t know, this is a dating website for Jews to meet, chat, and immediately start repopulating the earth with Jewish babies.  All Jews must use this website for a minimum of three months to please their mothers, and then they can move on to other sites.

I admit, I was a little disappointed when I first joined the site to find that there was not a very large selection.  However, there were a handful of prospects, so, like any good Jewish girl… I got cooking.  The thing about Jdate, is that when you grow up in a fairly small community, like I did, and then start dating as an adult in this community, pretty much everyone you date knows someone you know.  Jews call it “Jewish geography” but I am guessing this is not unique to us…

So I meet this guy, we will call him Moses (I know, clever).  Immediately I think to myself, Moses is about my age…. he grew up in this area…. someone must know him.  I mention him to a few close friends and sure enough, one of my best friends says “Sara, I know him, do not date him.”


When one of your best friends says “Sara, I know him, do not date him” ……. you should probably listen.

But no, “I have to give him a chance,” says Sara… “He’s probably grown a lot since you knew him,” says Sara… “I bet you are thinking of someone else,” says Sara.  

“No Sara, I am not, do not date him,” says friend.

But of course, I insist on going on this one date.  I usually make it a point to talk with someone on the phone before going out with them.  I like to hear what their voice sounds like, figure out if they can carry on a conversation… you know, begin the judgement process right off the bat (sad but true… we all do it).  My first sign that perhaps my friend was right should have been when during the second phone conversation, before the first date ever occurred, Moses said to me “would you like to go to a concert with me in October?”  Did I mention this phone conversation occurred in May?  My response was “how about we see how dinner goes first…..”  

Still, I had to go on this date.  

I get to the restaurant and Moses meets me outside and promptly pummels me with a hug.  Now listen, I am a very warm, touchy-feely, hug you all day long kind of person.  But this hug felt like I was being run over by a bear and all I could think was, “I think I am supposed to act really big and scary so he will run away.”  Isn’t that what you are supposed to do if you encounter a bear?  But I digress….

During the course of dinner, somehow the following conversation occurs:

Moses:  Do you think the man should always pay?

Sara:  No, I think it’s nice when the man offers to pay on the first date, but in general I think both parties should offer to pay.

Moses: Hmmm…

Sara:  (uh oh)

Moses:  You know what really turns me on?

Sara:  (Do I have my pepper spray?)  Uh…… no?

Moses:  Well… like… let’s say me and a girl… we are at the movies… and the girl… she steps in front of me and throws her money down on the counter for the tickets and says “I got this.”  That is such a turn on.

Sara:  (oh shit) Okay….

Moses:  Yeah… if that happened, I would be like, baby… let’s find a bathroom.

Sara:  (I definitely do not have my pepper spray)

Moses:  Ya know what I mean?

Sara:  (NO?!?!)  Uh… sure.  

Needless to say, I was not giving this guy a chance, he had not changed since my friend new him, and he was exactly who my friend was thinking of.

Oh well…. thanks for the memories Jdate.



For years people have been telling me…. you have to write about this.  The “this” they are referring to would be the dreaded DATING.  Honestly, I thought that the trials and tribulations of my love life were unique; that what I was going through over and over and over again was so crazy that no one else would believe it.  Turns out, there is a whole lot of crazy out there… and I have only dated, like, half of it.

I spend many nights wondering why I am 30 and single.  I am told that I am a reasonably good looking person with a good heart.  I make people laugh, I make people cry (oops), I am a loyal friend, passionate, adventurous, curious and when I love, it’s with my whole heart.  It is very easy to feel sorry for yourself in a world full of rejection.  But then I have to face the fact that I too reject.  I’d like to think that I only reject the truly crazy–like should be locked up crazy– but the reality is that my standards are high, just like everyone else’s.

About four and a half years ago I went through a bad break up… the worst break up yet (but I’m only 30 so give it time).  After that break up my best friend’s husband said something to me that he again repeated to me a few weeks ago.  “I fear that one day you will settle for a loser because you think too low of yourself.”  At the time of the breakup, maybe I would have.  Maybe I was afraid to be alone after being with someone for so long.  I think at this point in my life I know the answer is not to settle, but that means having standards… that means I have to reject too.

So does that make me a hypocrite?  To shout from the rooftops that I am READY FOR LOVE and WANT TO BE IN A RELATIONSHIP and then turn around and reject men who are genuinely interested in me.  To complain about how awful and hard dating is and how judgmental men can be… and then turn around and judge them right back… I don’t know, maybe.  

I have a million questions and few answers, but I am more than happy to share my experiences in this crazy world of dating (and I mean CRAZY) and maybe someday, the answers will come.

Happy Friday everyone.