Dating in your Thirties: Valentine’s Day Edition

It’s Valentine’s Day—a day that most men wish would permanently go away and also a day in which women tap their feet waiting to side eye their significant others when they’ve sent no flowers or chocolate, or made no dinner reservations. As illustrated below, Valentine’s Day can be equally frustrating for those of us dating in our thirties: 

What Do You Get Your Friend With Benefits?

I pick her up after her bartending job.  She smiles as she hops into my car and starts to make small talk.  I return a half-hearted smile and hope she doesn’t talk me to death—it’s late and I’ve had a long day at work.  We get to my place and I grab something to eat while she showers. I shower after catching up on the news and we both head to bed.  She leaves before morning.  This is our routine about two to three times a week.  We rarely speak other than when she comes over for what she calls “love making”.  She recently mentioned wanting me to hang out with her friends.  We all know what type of relationship this is—friends with benefits and nothing else (for me at least).  Now today is Valentine’s Day and I’m wondering whether I should get her something.  She is not my girlfriend nor will she ever be.  But she’s probably expecting something since we’re sleeping together, right? If I take her out will I be sending her the wrong message?  I don’t want her to feel bad, but I don’t want to mislead her either.  I don’t want to end this friends with benefits thing we have going and I’m worried that if I don’t acknowledge her on Valentine’s Day, then this might be it.

I Took You Out For Valentine’s Day–Now What?

We met in a coffee shop. Our encounter was brief but sweet.  We talked about the book I was reading and he recommended a book for me to purchase.  After a few phone calls he asked to meet me for a drink.  I was hesitant at first but decided to go anyway.  We shared a few laughs but I knew immediately that we could never be more than friends (I’m picky intuitive).  After a few flattering remarks about my beauty and enjoying our conversation, he asks when we can meet again?  I begin to stall, hoping he can’t see the anguish on my face.  “How about next Friday,” he proposes before I can think of a response.  I check my calendar to stall for some more time, and realize that Friday is Valentine’s Day.  “That’s Valentine’s Day,” I declare while trying to think of a quick response.  “So, it can be our first official date.  Wouldn’t that be romantic?” he replies.  I give him a blank stare until he uncomfortably changes the subject.  Am I wrong for not wanting to go out on Valentine’s Day with a man I don’t like nor want to be romantically involved with?  I don’t need a romantic dinner that badly.

She Trying to Pick Up A Valentine in the Club

The music is glaring and I spot her across the room.  She is making her body move like a contortionist and I can’t help but two step my way over to her so that we can rock to this “Drunk in Love” remix.  We dance to three more songs and I’m lost in her rhythm.  It’s almost like we’re the only ones in this club.  I ask to buy her a drink and with sweat causing her face to glisten slightly, she smiles and walks with me to the bar.  We try to have a conversation over the blaring music in the background.  I want to see her again, if only to move my body to the rhythm of hers one more time.  Before she walks back over to the sea of men on the dance floor, I ask to take her out.  “I would love to!  How about this Friday?”  As the words rolled out of her mouth, it was like the DJ brought the music to a frightening halt.  Did she say Friday? Valentine’s Day?  This chick wants me to take her out on Valentine’s Day.  As the dollar signs start rolling through my head like a slot machine, I tell her I’ll give her a call later in the week to confirm.  With my drink in hand, I walk over to where I was standing hoping to find another beauty who isn’t interested in a Valentine’s Day date.  Should you expect to be taken out for Valentine’s Day on a first date?

I sympathize with the pressures that this one day seems to carry for both men and women.  Valentine’s Day has always been a special day for me because it is my Ace’s birthday.  I am not fussy about presents, so I have never placed a lot of pressure on my significant other to go above and beyond on that day–I’ve always preferred that he demonstrate his love in simple ways throughout the year.  Whether you are bemoaning the day, or posting posting your gifts on Facebook and Instagram, take the time to remind those you care about how much you love them.

The Misadventures of Dating in Your 30s Part 2

As some of you noted to me in your e-mails, comments and Facebook posts, dating in your 30s (40s and even 70s) can be rough.  Part I of this series stirred up great dialogue about lessons learned, the importance of communication and questions about who should pick up the tab on a date?

My intent in writing these dating chronicles isn’t to dissect who is right and where things went wrong.  The goal is to find the humor in a situation that wasn’t so funny at the time.  But I always welcome your comments and opinions on these scenarios.  For those of you who are curious as to which of these were my experiences—technically they all were.  Because as my friends recanted the stories, I felt as if I was experiencing it alongside them.

Recreational Activities

I’m taking her out on our third date.  If I calculate all the money I’ve spent on this woman since our last two dates, she’s close to $250 (not that I’m keeping count). I order the chicken; she orders the steak—go figure. We make more small talk. Our food comes out and she uses her fork to penetrate the steak.  She asks the waiter to send it back–oh no not again! She now wants the fish instead. She has returned a portion of her meal during every date so far. Red flag? The waiter politely obliges. I’m not going to let it bother me this time because I’m focused on the big picture–my steadfast rule: if I’ve been spending money on you, I’m getting some by date number 3!  We enjoy the meal and have a fairly decent conversation. I like her smile, she’s pretty and she’s smart.  Despite her restaurant etiquette I’m starting to dig this woman.  We share a few laughs throughout our meal and I help her with her coat as we depart the restaurant.

We arrive at the front door of her place around 11:30PM.  I’m gazing into her eyes to see if she’s giving me a signal to park and come upstairs.  Before I could make a determination she asks, “do you want to come up for a little bit?”  I don’t hesitate and quickly demonstrate my superb parallel parking skills.  She lives in a five-story walk up—no wonder she stays in shape.  Out of breath I step inside and am greeted by a high-pitched howl—damn she has a dog!  I have a seat on her couch and she brings two glasses of patron and cranberry juice and asks, “do you smoke?” I reply, “nah, I don’t fool with cigarettes, you?”  She responds, “I mean weed silly!”  Feeling a bit goofy, I respond, “oh I tried it a couple times in college.”  Before I could say anything else she was back on her feet.  She returns with a contraption (I later find out it’s called a vaporizer) and two grams of weed.  She lights it up and passes it to me to take a hit.  I hesitate at first, but I tell her I’m good and decide to pass.

It’s 1:00AM and I’ve managed to position my hand on her leg.  She’s high and snuggled into my chest.  With one arm wrapped around my waist and the other hand holding tightly to the vaporizer, in a whisper, she asks, “have you ever tried coke?”  Okay I was just talking myself into getting used to the fact that she blazes on a regular basis.  But she does coke too? Weedhead is one thing, but cokehead?! Is it an occasional thing? Am I overthinking? Should I give it a try?

Little White Lie

I am ready to call it a night after being out at a club.  Since my car keys are in my friend’s car, I can’t leave until she gets in her last round of bootie shaking.  As I impatiently stand against the wall, out of nowhere he approaches.  We exchange pleasantries and he asks me whether (1) I have a boyfriend, (2) I’m single, or (3) in an undefined situation. I’ve never been asked the third option but I like his thoroughness.  The club is dim so I can’t get a good look at his face, but I can tell his body is attractive by his silhouette.  He tells me that he wanted to come over and say hello despite the very serious/mean look on my face.  I’m flattered. Mental note: stop mean mugging. Before he leaves, he asks for my number.  Should I give him my Google number or the real thing?  I will give him the real one since he seems polite, pleasant and pleasing on the eye.

He sends me a text message the next morning.  Damn, what happened to the 3-day rule? After a few exchanges, he calls.  In this new world of text messaging and tweeting, I appreciate a man who still picks up the phone to have a conversation.  We speak for hours on a variety of topics.  His peppering of questions demonstrates his keen interest in getting to know me.  The questions continue and I’m happy to answer honestly to give him insight into who I am.  I’ve already surmised by the many questions that he must have be a lawyer because I am feeling a bit interrogated—in a nice way.  We talk about his short term and long term personal and career goals.  He hopes to get married within the next five years and wants to land a job in the White House.  For a woman in her mid-thirties, his marriage trajectory is music to my ears!  I also like that he is ambitious.

As we’re talking on the phone I decide to search for him on Facebook to see whether we have mutual friends—DC is small, he may have dated someone I know.  He doesn’t come up in my search.  As I am logging into LinkedIn, he asks, “are you a big social media user?”  I tell him I use them sporadically, and ask him whether he uses social media.  Then I notice he has searched for me on LinkedIn. I’m not surprised, the internet makes it so easy for us to be nosey.  “No I’m not really much of a Facebook and Twitter user” he responds.  I ask, “so you’re not one of those who runs a Google search on people you meet?” He replies, “nope.”  I follow up by asking, “would you search someone on LinkedIn?”  He also responds “no”.  “Then why does my LinkedIn account say that you searched my profile a couple of hours ago?”  Damn damn damn! Did I just say that out loud?! Awkward silence.  He calmly says, “I didn’t search for you on LinkedIn.” Side eye. Did he just lie?! I said, “really? That’s’ not what LinkedIn indicates.” More awkward silence.  I switch the subject.   There goes my idea of him being amazing. Was I wrong for asking? If he can lie about this, what else will he lie about?

Inverse Relationship

I leave my favorite Thursday night happy hour spot feeling optimistic about the women I met tonight.  My swag was on 100, resulting in six phone numbers from some very attractive ladies.  The next morning I send them all the same text message: “good mrng. hope u had a good night. great meeting you.” Four out of the six respond. One of them follows up with a text message asking, “when will I see u again?”  After a few more text message exchanges, I focus my attention on her and she becomes my favorite of the six.

Our first date a week later was to see John Legend in concert.  She purchased our tickets and also treated me to dinner. Damn, I could get used to this! We sleep with each other on the first date.  Now that is what you call a new-age woman! Sex was aight but it didn’t last as long as I would have liked. A week later, a card with a gift certificate to my favorite men’s store is delivered to my office.  The card has no name attached.  Nah, this can’t be from her.  It is from her! We spend more and more time together. Within a month, I find myself calling her “baby.”  She’s not too clingy and she doesn’t ask me questions about trying to commit.  I’m feeling her style.  She laughs at my corny jokes, and constantly finds ways to do nice things for me.  She could write a book for all these chicks who are waiting on a man to spend a ton of money on them before they give the man some attention.

Six months pass and she still has the same ride-or-die personality.  But, I’m not sure I want to ride for her the same way.  Why am I hesitating? I’m ready to settle down.  I still frequent my Thursday happy hour spot and I am still talking to women and taking their numbers.  Some of them are slightly more attractive than her and they pique my interest.  I sleep with some of them. I should probably tell her that I don’t know if I can give her what she wants.  But she isn’t asking for anything–yet. I’m ready to settle down, I’m ready to find that woman I want to spend the rest of my life with.  She seems like the right person for me.  She caters to me.  She loves me.  Sometimes I can see myself with her long-term, and other times, I would be indifferent if she stopped speaking to me. She’s not it. How am I going to tell her? She likes me too much. I’ll just ride it out and not say anything.

A Woman’s Sex Conundrum: The Solution

I can be a bit old fashion as it pertains to certain things.  If it were up to me, a man would still show up to take a woman on a date dressed in a tie and carrying flowers.  Okay maybe that’s a bit extreme, but my point is, we have strayed pretty far from the days where men really courted women and both genders had a deep understanding of and respect for dating boundaries.

Fast forward to 2011 and women have entered the era of the sex conundrum.  Before I go any further, this post pertains to a specific category of women and is not intended to promote premarital sex.  Rather, it is food for thought to those who fall into Category #2 described below.

Women generally fall into two types of categories as it relates to sex.

No sex before marriage (Category 1)

“I’m glad we waited”

We all set different boundaries for ourselves and draw the line in the sand at different points.  Although I applaud respect those who defer sex until marriage, it is not my reality.  Therefore, the following commentary does not apply to those who fall into this category and have chosen to wait until marriage before ever having sex.

Sex before commitment (Category 2)

Many women fall into this second category.  Instead of waiting for a marriage commitment, we have chosen to engage in premarital sex.  We are comfortable with this decision but have sometimes found ourselves questioning and/or regretting our choice of sexual partners.  Sex for women who fall into this category oftentimes occurs prior to determining the direction of the relationship.

In 2011 women who have sex without commitment have found themselves in what I refer to as the sex conundrum.  I specifically use the term commitment rather than the word marriage because oftentimes sex occurs prior to an expressed commitment of any kind or establishment of an exclusive relationship.  In this era of female empowerment women feel more comfortable in straying from traditional social norms.  But have we strayed too far from our best interests?  Have we convinced ourselves that we can freely have sex with whomever we desire, under any circumstance with little to no consequences?  Women (with men as their enablers) have created a sexual conundrum for themselves.

Some women believe that they can have sex with a man without an established commitment or emotional fulfillment.  They believe that their natural sexual desires can be satisfied without any emotional consequences or requirement of their sexual partner to want them beyond the act of sex.  I strongly disagree with this notion.  The only women who are able to rid themselves of any emotional draw to their sexual partners are prostitutes and women who are suffering from deeper personal issues and use sex as a means to mask/soothe those issues.  In other words, women generally lack the ability to have sex with a man without developing some emotional connection/feelings toward him.  The woman who consents to sleeping with a man after she is made aware that he does not want a commitment from her will still develop feelings for this man.  The woman who has a boyfriend/husband but decides to sleep with another man solely for sexual gratification will eventually develop feelings for that man.  The woman who convinces herself that she can remain emotionally detached from the man she is sleeping with is fooling herself.  Therefore, the problem usually arises when women sleep with men before having clearly established a mutual understanding of their relationship.

When is the appropriate time (for a category 2 woman) to sleep with a man?  I took an unscientific straw poll of my male friends prior to penning this blog and almost all the men believed that the best time was whenever the woman was ready, but preferably sooner rather than later—-generally within the first two months of dating.  But when I asked the men whether they were always prepared to commit to (i.e., date exclusively) the woman during this time, the general consensus was—no.  So if a woman almost always develops an emotional bond to a man once she has sex with him, and if a man isn’t willing to commit to a woman in the time frame that he expects to have sex with her, then how do we reconcile this?

Ever wonder why Michelle seems to have gone stark crazy over Sean even when Sean is not her boyfriend/husband? She calls him 100 times for the day, she slashes his tires and keys his car because Sean hasn’t returned her calls; she is standing outside his home screaming profanities to express her anger at the way she was treated.  99 times out of 100, whether she recognizes it or not, Michelle’s heightened frustration is because she has slept with Sean.  Herein lies the sex conundrum!

This problem can be rectified with a few simple steps.  Women should refrain from sleeping with men until they have had a discussion with their sexual partner and feel comfortable that he will embrace the emotional desires that will emerge once she has slept with him.  In other words, women must recognize and become honest with the additional demands they will likely place on their partner after they have sex with them.  I am not condoning the act of dangling sex in front of a man’s face like a carrot in order to get what she wants.  But it is important for men and women to recognize the depth of emotion that sex has on a woman (and sometimes men as well) and both parties must be prepared to handle the change that will inevitably come if a commitment is not established before sex occurs.

Within one to two months of meeting a woman most men aren’t prepared to answer the question, “where is this going and what are your epxectations” (and I doubt that a woman can be sure of her answer within this time frame as well).  Therefore, the best solution to this unidentified problem is…….wait for it…….women should wait until they have a clear understanding as to the expectations and goals of  a man prior to sleeping with him and men should start thinking about their own expectations of  a woman as they contemplate the idea of getting the woman into bed.  Men and women have sex too early in their “relationship”.  What is the requisite amount of time that a man should wait and a woman should hold out?  As long as Sean is unsure of how to answer the question “where is this going and what are your expectations” Michelle should refrain from sleeping with him because she will quickly become weary of Sean’s inability to answer that question once she sleeps with him.  On the flip side, men should not provide a woman with a false hope of something more than sex simply to get a woman into bed.  Her heart is attached to her body, so if he wants her body he must be prepared to take her heart as well.  A man should consider his desire to sleep with a woman in conjunction with his desire (or lack thereof) to commit to her.

The new-age concept of “friends with benefits” is a fallacy for a woman.  Maybe it’s time to revive the days when a man wrote a note asking “do you want to go steady? check the box” before he expects a woman to sleep with him.