First dates: What are the rules of engagement?
by e. lyle henderson-lassonuttvenshsky
“I just wanted someone to love, so I became a victim for someone to love.”
Grace Jones – Someone to Love – 1989
Rusty. That would best define my current dating practices. By choice, it has been nearly two decades since I last went on a date. I was chasing dreams and goals while establishing a solid foundation in my career and business. As I reflect, the years have mostly been a pleasant experience until now. I’m ready to date again.
Many seasons have come and gone since my last intimate encounter. A close friend inquired the other day insisting that it was time for me to conquer the inevitable and get back in the game – dating and searching for the ultimate, the right life mate. After all, time continues in spite of our own ways, and I have to face the inescapable, I am not getting younger.
Many seasons have come and gone since my last intimate encounter. A close friend inquired the other day insisting that it was time for me to conquer the inevitable and get back in the game – dating and searching for the ultimate, the right life mate. After all, time continues in spite of our own ways, and I have to face the inescapable, I am not getting younger.

With the advent of social media, to which I do not necessarily subscribe because I am . . . just fearful of all that it is and can be, I will have to jump in the hot seat and see where it goes. Then again, as a mature man, I am not one to go to clubs and bars either. Further, I was never a big fan of the scene although friends would frequently drag me out to socialize and partake of the flavor. I was always the designated driver to take care of them when the alcohol beat them down at the game of chance.
Almost daily, my dearest friends are unyielding in reminding me that my biological clock was ticking forward, not backward; and if I felt the urge for a meaningful relationship, I should probably find an opportunity to place myself in the presence of potential suiters. So we began a serious conversation about how I would go about finding the most optimal options.
Recalling the stories that many of these same friends have shared regarding meeting their partners, and for some, friends with benefits, and the first dates over the years, I realized that none of those stories were appealing to me. But I was willing to receive counsel and develop a plan of action.
I can’t fathom going to bars or clubs, still public places like parks and bookstores are not an option either. The grocery store merely gets a head shack and laugh, at best. So where does a seasoned man of substance and stature go to meet and greet. To find out, a dinner party would be the most enticing event to get a few of my friends, ten to be exact, together for session one to learn the contemporary rules of engagement when it comes to dating. In total, eight men and two women. Four of the men made up two couples, while the women, also, were a couple. The other four men, well, they could best be described as wild and free.
Almost daily, my dearest friends are unyielding in reminding me that my biological clock was ticking forward, not backward; and if I felt the urge for a meaningful relationship, I should probably find an opportunity to place myself in the presence of potential suiters. So we began a serious conversation about how I would go about finding the most optimal options.
Recalling the stories that many of these same friends have shared regarding meeting their partners, and for some, friends with benefits, and the first dates over the years, I realized that none of those stories were appealing to me. But I was willing to receive counsel and develop a plan of action.
I can’t fathom going to bars or clubs, still public places like parks and bookstores are not an option either. The grocery store merely gets a head shack and laugh, at best. So where does a seasoned man of substance and stature go to meet and greet. To find out, a dinner party would be the most enticing event to get a few of my friends, ten to be exact, together for session one to learn the contemporary rules of engagement when it comes to dating. In total, eight men and two women. Four of the men made up two couples, while the women, also, were a couple. The other four men, well, they could best be described as wild and free.

Over a three-course meal that included desert and plenty of enticing libations that assisted with dismissing any guard any of the guests may have had, the conversation began. It began to get a bit confusing as each had their own say. Still, they each were relentless in proclaiming their opinion was the best. One of the single men, would cast the bomb that silenced the room, stating, “You know you are going to have to put out. How are those skills?” I was floored and broke into a sweat. Clearly the dynamics of the conversation were altered.
“Put out,” I exclaimed looking like a dear in headlights. “I am willing to have a Dutch date and pay my own way.” Of course everyone looked at me as if I was an alien who just landed. “Now you know that is not what we are suggesting,” exclaimed another. The conversation, although a bit uneasy, continued. We decided to weigh the options of engaging in intimacy on the first date or not.
I would quickly learn that dating has changed significantly over the past two decades. Gone, it would seem, are the expectations of prolonged courtships with a hug and gentle kiss, maybe, as you left to go your separate ways following an initial meeting. Rather, in today’s dating marketplace, I quickly learned, it is potentially a kiss good night and never shall the two meet again; or right to the bedroom. Still, I found that having sex on a first date is not necessarily a relationship deal killer. Just because one has sex right away does not mean that one can’t achieve a long-term relationship in the end. Two of the couples were testament that sex on the first date could lead to long-term bliss.
“Put out,” I exclaimed looking like a dear in headlights. “I am willing to have a Dutch date and pay my own way.” Of course everyone looked at me as if I was an alien who just landed. “Now you know that is not what we are suggesting,” exclaimed another. The conversation, although a bit uneasy, continued. We decided to weigh the options of engaging in intimacy on the first date or not.
I would quickly learn that dating has changed significantly over the past two decades. Gone, it would seem, are the expectations of prolonged courtships with a hug and gentle kiss, maybe, as you left to go your separate ways following an initial meeting. Rather, in today’s dating marketplace, I quickly learned, it is potentially a kiss good night and never shall the two meet again; or right to the bedroom. Still, I found that having sex on a first date is not necessarily a relationship deal killer. Just because one has sex right away does not mean that one can’t achieve a long-term relationship in the end. Two of the couples were testament that sex on the first date could lead to long-term bliss.

To address the big elephant in the room, my guests and I addressed the pros and cons of my trek back into the dating scene. That said, the decision depends on the end goal and how I would feel the morning after. I am not one to feel vulnerable or emotionally invested immediately. Regardless of the season, or the time that has lapsed between my last dating experiences, I would probably choose to wait for intimate relations.
It was interesting to learn during my investment in a non-scientific survey of my ten friends that six actively require sex on the first date to gauge whether to pursue or dismiss the ideas of another date. Ultimately, those that expect an intimate encounter feel it is a pathway to a relationship. The issue seems to be that the initial high of the first date and night of sex doesn't maintain the excitement and vigor of the actual relationship going forward. I learned from the conversation that many experienced anxiety and second-guessing following sexual encounters, although, in their minds, it is a requirement.
It was interesting to learn during my investment in a non-scientific survey of my ten friends that six actively require sex on the first date to gauge whether to pursue or dismiss the ideas of another date. Ultimately, those that expect an intimate encounter feel it is a pathway to a relationship. The issue seems to be that the initial high of the first date and night of sex doesn't maintain the excitement and vigor of the actual relationship going forward. I learned from the conversation that many experienced anxiety and second-guessing following sexual encounters, although, in their minds, it is a requirement.

Interestingly, one of my guest shared that for him nothing compared to the anticipation and thrill of a first date, and the possibilities for a conquest. It is the newness of the adventure. Obviously, the feel and sensation of meeting and greeting a potentially new suiter send delectable shivers down one’s spine with the unyielding ideas of possibilities. For him, the excitement of getting frisky entices even more with the end result being the highlight of the evening’s event – sex.
Still, I learned that one advantage, among many, for first date sex is to get a good feel of how the partner is in bed. Clearly it is obvious that most take this first action as a prelude to other things, including the possibilities for a long-term relationship; after all, there are those who simply don’t want to mingle with someone who can’t deliver and “bring the goods.” In short, it is better to know early on if the partner is capable of performing well in bed than to wait until later in the relationship when it could be harder to end everything.
Then again, there is definitely a negative side as well: one being the fear that once you give in, you will be regarded as “easy”. The rest is clear. Still, there are others who are apprehensive about the morning after having sex—let’s face it: very few people look just as good in the morning as they did the night before. Another downside to this dilemma is when the partner may actually be worth it – it’s infinitely better to get to know them better first than to lay everything out on the table the first chance you get.
For some, sex is simply a sort of a release, and it may or may not lead to any kind of commitment. There are some who may lose respect for a potential mate after they get what they want; because they simply assume that it is something that is usually done on every first date, regardless of who one may go out with. In this case a buddy with benefits seems to work.
Having sex on the first date is not an unusual phenomenon, probably because of the heavy emphasis that is placed on it by many people in society. However, not everyone is keen to the idea, and so a lot of people always debate the issue. Is it right to have sex on the first date? Should two people engage in sexual intimacy even if they have only met two hours ago? Actually, there is no question of whether it is right or wrong – it merely is.
The lesson learned for me is that it is better to know early on if the rules of engagement on the first date include the anticipation or expectation of sex. Actually, this burning question is better answered when considered on a case-to-case basis, since it is often a value judgment that mirrors the double standard that society has with regard to sex, and healthy sexuality particularly. Sadly, the gender and orientation difference that usually dictates the situation is not even taken into account. Sex on the first date has both advantages and disadvantages. Consider your own values and make a more conscientious and educated decision should this particular situation ever come up in your life.
Conversely, as for the four dinner guests who subscribed to waiting, the key is establishing a foundation for friendship that grows into an emotional connection and possibly love. When each are ready to explore the more intimate sides of their nature, it will be revealed. Each shared the notion of making love as the ultimate connection between two partners, rather than engaging in sex merely to fulfill a physical need. That can only be established after knowing and caring for the other. A deeper bond between two individuals rather than just casual associates. One described the act as a deeper emotional and physical declaration of a union and trust for one another.
I'm not sure what I'm trying to prove other than that in my experience things that have been inconsistent when it comes to potentially dating and when sex occurs. I can't say one is good and the other is not...it just is. I live and operate in a non-judgmental zone. So when the feeling is right, go for it. If you want to wait, then by all means it’s a personal choice. Never feel pressured into doing something you aren't comfortable with and things should work out more often than not.
e. lyle henderson-lassonuttvenshsky is a communication strategist and writer living and working globally from the mid-Atlantic area.
Still, I learned that one advantage, among many, for first date sex is to get a good feel of how the partner is in bed. Clearly it is obvious that most take this first action as a prelude to other things, including the possibilities for a long-term relationship; after all, there are those who simply don’t want to mingle with someone who can’t deliver and “bring the goods.” In short, it is better to know early on if the partner is capable of performing well in bed than to wait until later in the relationship when it could be harder to end everything.
Then again, there is definitely a negative side as well: one being the fear that once you give in, you will be regarded as “easy”. The rest is clear. Still, there are others who are apprehensive about the morning after having sex—let’s face it: very few people look just as good in the morning as they did the night before. Another downside to this dilemma is when the partner may actually be worth it – it’s infinitely better to get to know them better first than to lay everything out on the table the first chance you get.
For some, sex is simply a sort of a release, and it may or may not lead to any kind of commitment. There are some who may lose respect for a potential mate after they get what they want; because they simply assume that it is something that is usually done on every first date, regardless of who one may go out with. In this case a buddy with benefits seems to work.
Having sex on the first date is not an unusual phenomenon, probably because of the heavy emphasis that is placed on it by many people in society. However, not everyone is keen to the idea, and so a lot of people always debate the issue. Is it right to have sex on the first date? Should two people engage in sexual intimacy even if they have only met two hours ago? Actually, there is no question of whether it is right or wrong – it merely is.
The lesson learned for me is that it is better to know early on if the rules of engagement on the first date include the anticipation or expectation of sex. Actually, this burning question is better answered when considered on a case-to-case basis, since it is often a value judgment that mirrors the double standard that society has with regard to sex, and healthy sexuality particularly. Sadly, the gender and orientation difference that usually dictates the situation is not even taken into account. Sex on the first date has both advantages and disadvantages. Consider your own values and make a more conscientious and educated decision should this particular situation ever come up in your life.
Conversely, as for the four dinner guests who subscribed to waiting, the key is establishing a foundation for friendship that grows into an emotional connection and possibly love. When each are ready to explore the more intimate sides of their nature, it will be revealed. Each shared the notion of making love as the ultimate connection between two partners, rather than engaging in sex merely to fulfill a physical need. That can only be established after knowing and caring for the other. A deeper bond between two individuals rather than just casual associates. One described the act as a deeper emotional and physical declaration of a union and trust for one another.
I'm not sure what I'm trying to prove other than that in my experience things that have been inconsistent when it comes to potentially dating and when sex occurs. I can't say one is good and the other is not...it just is. I live and operate in a non-judgmental zone. So when the feeling is right, go for it. If you want to wait, then by all means it’s a personal choice. Never feel pressured into doing something you aren't comfortable with and things should work out more often than not.
e. lyle henderson-lassonuttvenshsky is a communication strategist and writer living and working globally from the mid-Atlantic area.
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