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Sex on the First Date  Great Time or Bad Decision?

As I mentioned in my earlier follow-up to the posting “Sex in the Early Dating Stages Sex on the First Date: Too Soon or Just Right” I had written a Sexploits article discussing two examples of sex on the first date.  I wasn’t going to publish it after some recent events changed my original feelings on the subject; however, I decided that I would still publish it in it’s entirety with a preface.

Up until very recently, I had believed sex on the first date was capable of leading to meaningful relationship in certain instances where there was extreme attraction or a major connection despite the fact that it breaks the number one girl rule.  However, after extensive reflection, I’ve reevaluated and changed my opinion.  I think maybe 1 in 100 or realistically 1 in 1000 pairs who have sex on the first date wind up in a relationship.  Plus, you have to assume that sometimes sex happens on the first date because of a prior friendship or at least the two individuals knew each other for some time before the first official date.  In those instances it is still technically still  first date sex but the prior connection definitely allows for an increased probability of relationship success and thus the stats are likely skewed.  Factoring out such instances I would surmise that perhaps 1 in maybe 2000 cases of sex on a first date result in a subsequent relationship that extends beyond one or two dates.

In the examples below I clearly believed that friendship and sex can mix successfully.  I still haven’t ruled that out and feel that friends with benefits is an acceptable, workable scenario for certain people (I am bound to do a post on this topic sometime in the near future); however, it is extremely tough when one person has feelings and the other doesn’t.  I made the mistake of falling for one of them very quickly and cared about him deeply, as frustrating as that is to admit.  But, I will swallow my pride and acknowledge that I allowed sex to cloud my judgement and developed feelings in a friends with benefits scenario.

In my defense, we dated first and he decided he didn’t want a relationship– he wanted all the benefits without any of the work.  But, I was already hooked, so I gave myself up without requiring anything from him.  Sure, I got great sex out of it but when I would leave the next day the happiness and high would fade into tears and loss of self worth.  I’m not saying there is anything wrong with what I did in the general sense; yet, I compromised my morals and sacrificed what I wanted to be with someone who didn’t want me beyond physicality simply because I liked him so much that I would be with him in whatever way I could.  It wasn’t healthy and it drained me over time, but we all do crazy things when we think we are in love.  Then one day we realize we were in love with an idea, not a person, and that we’d allowed our judgement to get clouded by lust.  Pheromones, hormones, endorphins, and racing thoughts had taken over our minds and impaired us from having rational thoughts about the man we liked.  We think about him when he is not around and “fill in the blanks” on conversation as well as daydream about future times together.  Then, before we know it, we’ve lost site of what was real and what we just wished was.

It’s a sad reality but the power in a relationship lies with the one who cares the least.  If I didn’t want to hook up with this particular guy anymore, ignored him, or just stopped talking to him he probably would not have cared and would have moved on to the next.  Yet, when he ended things and cut his ties with me I cried.  Obviously this stems from something deeper than this boy and gets to the root of my self-esteem issues that started with my family, were exacerbated by my peers growing up, and still exists in my adulthood much to my dismay.  I would love to be able to radiate confidence, careless about the men who don’t want me, and just appreciate what I do have and I work on that everyday.  But it will take time to erase 25 years of mental brainwashing and paranoid thoughts.  I have made progress and certainly know my strengths; however, when someone I like and care about gets upset with me, doesn’t feel the same about me as I do about him/her, or ends things, my fear of abandonment and loneliness creeps back and I inflate the situation in my mind.

However, enough about my neurosis and issues, here are my two sexploit examples of sex on the first date and I would love to hear stories from my readers.  You can post them below or if you want them posted privately/anonymously please feel free to email them to me at

There are two personal examples of sex on the first date that I can share which illustrate when it is a bad decision to sleep with a guy so soon and when you can do so without regrets.  Neither resulted in a long term, committed relationship but both experiences were followed by additional dates.

On my first date with “A” he took me out on Saturday night—a prime date slot.  We went to a fancy Italian restaurant and spent a few hours having dinner, drinks, and good conversation on a roof deck one summer evening.  There was chemistry both physically and interpersonally and I was comfortable being myself, which is not always easy on a first date.  The conversation was so honest and open and we shared stories about our past and learned what we had in common and where we differed.  He conveniently spilled some sauce on his shirt and wanted to change before we went out for more drinks and small talk.  Needless to say, we never made it back out until the next afternoon.   Not wanting to have sex on the first date, I took precautions to help me in my mission to restrain from physicality.  I had met him before the date as he and I share mutual friends.  After spending a sex-free night at his place on this prior occasion thanks to an embarrassing overconsumption of alcohol resulting in a night of illness, I went into my first actual date already highly attracted to him.  So, I valeted my car to ensure that I would not spend the night.  FAIL.  We made out for hours as I continued to resist his charm and attempts at getting me into bed.  Eventually he broke my willpower and we had sex—great sex, multiple times.  We spent the night together continuing to get to know one another and I left the next day with a smile on my face and decided that whether this went anywhere or not, I had fun.  To this day do not regret it.  While we never ended up in a committed relationship, he actually remains a good friend of mine.

My first date with “Z” was on a Thursday and there was no real set plan.  He picked me up and we drove around to find a restaurant.  We had a good conversation over dinner and I found it cute that he seemed to be a little nervous.  He did the right things like opening the passenger door to his car for me and telling me I was beautiful.  Despite this and the fact that he was hot, I was somewhat ambivalent about him.  I would have been fine with him going home after dinner with a peck on the cheek and maybe seeing him in a week or so.  Yet, he invited himself back to my house and since I felt like I still had control over the situation and wanted to talk to him more, I agreed.  We chatted for a while and got to making out.  I refused to let it go farther for hours and made sure our clothing stayed on and repeatedly said that this was a first date so it was not going to go any further.  Eventually we had sex because I gave up fighting it and rather than uncomfortably ask him to leave, I gave in for all the wrong reasons.  I was not overwhelmed with passion and honestly I was indifferent about the entire situation—a giant sign that we should not have hooked up.  To make matters worse, it lasted about a minute and was not gratifying.  At first I thought that I could be fine with it but after lying down and trying to go to sleep I started to have buyer’s remorse.  When he left early the next morning I Googled BPD and Biopolar disorder, convinced that this risky sexual behavior was symptom of some mental disorder.  I went into work the next day shaken up.  I obviously got over it not too long after and actually went out with him again but it never really went anywhere and he turned out to be completely wrong for me.

With “A” I broke the no sex on the first date rule because certain criteria that allowed for rule breaking was met and the attraction was so strong that despite the potential negative consequences, the benefits were worth the risk.  In this case there was no regret because the outcome was positive, the sex was gratifying, and there was a connection that warranted giving in.  However, with “Z” I did not really choose to have sex so much as I chose to allow him to have sex with me out of an inability to assert myself.  I suppose that I also was afraid that if I turned him away he would never want to see me again and I was in a place where I could not handle rejection.  Since hindsight is always 20/20, the sex was an all-around bad idea.  Maybe if the sex had been great or I had slept with him for different reasons I could have justified the unwise and out-of-character actions but we can’t live in a world of maybes and what ifs.  The past if the past and you can’t take back sex.

Since my sentiments above about my sexperiences going for home on a first date are based on how I felt about the sex after the fact, the two examples may not seem to engender any wisdom.  However, there was something to be learned out of both experiences.  Personally I learned that waiting a few dates works best for me and that I have certain self-enforced directives that I need to abide by.  I have personal morals to follow and certain exceptions to my rules; but, for the most part, casual sex is just not something I’m capable of—at least not with a stranger or person whom I barely know…friends with benefits is a whole other topic.  I am sure that a lot of people are like me and while they ultimately go into a first date with their self-regulations and preconceived notions, there is always the small possibility that it may go physically further than planned.

Having broken my rules in the two examples above, I learned the hard way that the reasons for the sex make all the difference when the dust settles.  If there is passionate attraction and a strong connection that might be enough to compromise your personal ethics but make sure you are fully aware of your reasons for having sex so soon and are mindful of what your intentions with this person are.  If you are looking for relationship potential, you may want to hold off on the first date sex.  However, I have also learned that sometimes objectives do not match outcomes even with the best laid plans and if a guy is capable of a relationship and feels a connection to you, first date sex probably won’t be a deal breaker—but you have to ask yourself if you are willing to take that risk.  So while I don’t really believe in regret, I do wish I could take back the latter story.  In the case of the former, I know the outcome would not have been different and I had a great time; however, there is a small part of me that will always wonder “what if I waited with him?”  While I accept that I cannot change my actions for that day or get an answer to my question, it does not really make the question go away.  Ultimately, all I can take away from the experience is a +2 to my number and a better understating of myself.



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