Dear Megan,

Sex on the first date. Is that a terrible idea? If I did that, (I did), will it ruin my chances of this guy seeing me as long-term potential?

I feel grossed out that I did it. And his interest seems waning. Afterwards, he did ask if I wanted to join him at a party he originally told me about the next night. I wasn’t free to go and he hasn’t put much effort into texting me since. He’s very attractive, and I wonder if I’m not attractive enough for him, or if I was just too easy to sleep with.

Right now I feel terrible. Unattractive, easy, and cheap. I want to dig a hole and hide inside it.

Please help!

Sincerely yours,

-First Date Floozy

Dear “First Date Floozy,”

Wow… Dare I touch “sex on the first date” with a ten-foot pole? Or should I just use a ten-inch one and see if you can handle it, you saucy little minx. Hahaha. BOOOMMMM!!!! Just kidding… I couldn’t resist. (That’s what she said.) Okay, last one. But, seriously, let’s everybody calm down, take a deep breath, grab some wine, and pull up a chair, because when it comes to sex things are about to get a whole lot easier…

To begin with, let me just say that I’ve known some fantastic couples who slept together on the first date and have been happily together – (keyword: “happily”) – for over twenty-five years. I’ve also known some couples who have been together for just as long but did not. So, as far as I’m concerned, sleeping together on the first date does NOT ruin the potential for a long-term relationship.

BUT, can it be a terrible idea?

Well, sometimes…

Sex is a terrible idea one time, and one time only: when you know doing it won’t bring you joy.

(Well, technically, I should probably add when you don’t take the proper precautions when it comes to protection… You’re welcome, Planned Parenthood.)

And how will you know for sure when sex won’t bring you joy? Why, the same way you came to know everything else you know in life, my dear: Experience.

“In life I’ve had to figure out – on my own terms – what works and what doesn’t. And I’ve have years of practice.” –Drew Barrymore

While most of us don’t have a crystal ball that will tell us if a connection will last forever, (regardless of whether we wait three dates, three weeks, three months, or three years to sleep with a person), we all have an emotional guidance system that will let us know when it’s time to have sex. But, the only way to tap into this mysterious “know-it-all” machine is to first get out and live.

Allow yourself to have experiences that create contrast – (i.e. “Things that feel good” vs “Things that feel bad”). And spoiler alert: life will sort of take care of this one on its own… Whether we want it to or not. (Sad face.)

Then, you’ll want to spend some time alone sifting through the emotional data you’ve collected from said experiences and reflect.

(Mmmm…. Namaste… )

Your natural desire to feel good will help you define what it is that you want from the experiences you’ve had, (i.e. reveal your authentic self), as well as help you create boundaries against any distractions from you living your best life.

And, last but not least, you’ll want to turn around and care soooo much about how you feel that you’ll decide to only do more of what feels good and less of what feels bad.

The self-discipline involved in the last step can be tough at first, but it’s absolutely crucial in honing your skill in quickly, (and eventually effortlessly), following your emotional guidance system’s “yellow brick road” of positive feelings. For every time you honor the emotional data you’ve collected from your experiences, and stick to what feels good, you’ll be rewarded with something else that feels even better. And that, my friend, is what will allow you to establish the trust you need in your emotional GPS system to handle situations like the one you were in like a Jedi, instead of a Regretful Randy. (Which is a term I just made up… and am pretty proud of).

Right now it’s impossible for you to know just yet whether sex on the first date is appropriate for you because – (follow me now) – you’ve blocked off your ability to properly digest what the information a sexual experience like this has to offer you by getting caught up in the (false) beliefs that: (1) you should already know how an experience will make you feel before you experience it, and (2) that that there’s an appropriate time for you to have sex that can be dictated by someone other than you and your experiences. (Whew!)

Consequently, the negative emotions you’re currently feeling, doll, isn’t due to your emotional guidance system agreeing with you that you’ve done something wrong, it’s due to your emotional guidance system letting you know that there is no joy for you in adopting someone else’s opinion on what you do, or don’t do, with your vagina.

Relief in this moment will come when you accept the fact that you’re on a journey to learn what works for you; and THEN, and only then, will you be free to receive the insight you seek from what your experiences have to offer you.

This insight will let you know under which circumstances having sex will feel good. It will let you know what needs to be in place mentally, spiritually, and emotionally for you to get your emotional guidance system’s “it’s safe” signal and gleefully get your freak on.

And, finally, if you want long-term potential with someone who will accept you for you, the answer, again, lies in you getting comfortable “doing you.” (No pun intended… Or is it… He he he.) That means that your authentic match will respect you and your desire to have sex whenever the hell you want to. Not when society deems it appropriate.

The right guy for you will be okay with whatever circumstances you enjoy having sex under. Those circumstances could be created right away, take longer, or vary. It all depends on you, and how you feel.

So, until then, keep sifting and sorting through life and getting to know yourself; and best of luck giving a f*ck, or not giving a f*ck, along the way.

-Megan 🙂

For my story check out “The Care and Feeding of Sex Symbols” here

To submit your question to “Dear Megan” click here!

“Dear Megan” Home Page

To Subscribe to my YouTube channel click here!

Note: As this column is designed to be a judgement-free zone, only those who have been, (or know someone who has been), in a similar situation are invited to comment; especially if the question is unorthodox or hard for one to relate to. And for even more relevant insight, those seeking answers are always encouraged to go within.