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.