Guest Column: Dating Online Series. Men & the Moments? Part I

by Ms. Jennifer

Home from the holidays was sorta like the roller-coaster of online dating only on steroids. Returning to Chicago is always bittersweet since I spent most of my adult life there and assumed it would end there.

Seeing my two kids is always very satisfying and now there is added excitement since my son got engaged. There was a little wedding drama since I wasn’t invited to go dress shopping and then later not being allowed to go invitation shopping because my ex is sorta dating the woman who works at the store.

Some bitch is going to prevent me from spending the few days I have with my son in wedding planning bliss(?)  Being told what I can and can’t do never goes over well with me. Still I mostly behaved myself… I tried to pick up a guy who owns an art gallery while waiting on the three of them (my ex, my son and his finance) thumbing through wedding albums. Weeks later I’m still not amused by some woman who works at Hallmark calling the shots because presumably she’s uncomfortable.

Well, if that’s how this is going down then I ain’t comfortable with her coming to the wedding!  Ok, enough of that, the truth is my son and his fiancé are extraordinarily capable and they don’t “need” me to help pick out the wedding invitations.  My son understood rather quickly it’s not really about being needed, but rather simply feeling involved in such a milestone event (in the end I did get to go dress shopping to help break the tie between two gorgeous wedding dresses).  Maybe not having a little shitfit worked to my advantage after all.

After Chicago came California where my daughter lives which takes all day to get to. I rendezvoused with my brother and sister and this is where the story goes south.  How can I explain in one sentence the insanity?  Here we were in a remote and beautiful spot of heaven on the northern coast of California celebrating my daughter’s grown up life and the new year and all my siblings could do was bitch and complain like some old married couple.  I’m embarrassed to tell you how bad it was.  Reminder, it was a herculean task to get my dad to the nursing home 80 miles away from my house and coach some dude on how to take care of my dog while I was gone.  What exactly did they have to bitch about…everything.

By the time we hopped in the rental car to leave after spending close to a week together, I had it with both of them and I decided to let them have it.  Let’s just say this didn’t have a happily ever after ending. I probably should have picked up some duct tape at Home Depot.  My daughter was acting 1000 times more mature than both of them.  I told her she had enough material to write a long essay in her psychology class on family dysfunction.  It was so bad I was almost looking forward to picking up my, piss on the floor, dad.  When I went to pick him up he had exactly two articles of his clothing remaining (I packed a week’s worth), and was bruised and congested.  They call this respite (?)

Once I settled back home I knew I needed to light a fire under my dating life which had completely gone on hiatus (except for falling in love with my perfect match who lived in Chicago less than 5 miles from where I used to live… sigh).  To make up for lost time I had five dates lined up (only one bailed!).  I actually had a double header last night and hit a home run!  The only two little problems rolled into one big problem with Gregg, but let me tell you about my first date with Alex.

Alex juggled around my dance class and then my caregiver running late and despite his flexibility, I started to get this gnawing feeling in my stomach.  After bouncing around where to meet, he ended up running late, but I told him not to worry I had a book. I was sitting on the porch when he pulled up in his white Mercedes or was it a Porsche? When he came up the stairs and greet me I remember the feeling of him standing too close and hovering in my personal space. He’s one of these guys who when he enters a room needs some sort of service.  At first we were going to sit at the bar and then next we were at a table. He made sure the waiter knew we were there ONLY to order drinks.  I got the message.

Alex told me he was vain and that he didn’t dye his jet-black hair. He’d just come from tennis practice and looked good in his jeans and shirt. He proceeded to tell me all about himself a combination of ego (rich and successful) sprinkled with a little bit of hippy.  Eventually, he asked me about myself and I let him know I wasn’t like the high maintenance girls from his past. When you have that much money why commit to anyone just buy yourself a trophy girlfriend? I’m not that. Maybe I’m not being fair, but he talked a lot about  money and women’s equality (so they could pay their own way, but he forgot to take into consideration the huge disparity between our net worth). On principle I offered to pay my share (I didn’t want to be like the woman he told me about who order half the menu and then handed him the bill), he had me pay the tip.

When the interview was over he gallantly walked me to my car and leaned in for a kiss.  Am I the only one just now figuring out how much you can glean from a kiss?  It was a straightforward kiss slightly aggressive, but there was no shading, no nuanced, nothing subtle about those lips. So will this “hippy” call me back?  I’d give it about a 10 percent chance that I will hear from him again.

The timing was perfect as soon as I said goodbye to Alex, I hopped in my car to meet Gregg. Now I don’t recommend being a dating slut (which I’m doing for the experience/adventure, not a free meal besides 98 percent of meet and greets are at most one drink). What if I was in love with Alex and didn’t want to leave, but honestly that seemed so unlikely I took my chances, plus I have to work around when I have a dad-sitter so I have to cramp things together because it’s hard to find caregivers who want to work nights (except recovering drug addict who are desperate for work and you only hope don’t relapse and clean you out).

What I totally wasn’t expecting was to fall in love with Gregg. He told me “you have the best profile I’ve ever seen.” Still, I couldn’t get serious about this guy.  His profile was very clear that he travels the world and was never home, besides he lived in New York.  Now what am I going to do about this little problem?  How many dates have I been on where it’s just wasn’t there?  Was this some sort of cosmic joke or bad dating karma? Maybe the silver-lining was it might show me how to be flexibility and stay in the moment– something my hunker down-where are we going- brain struggles with.

By this point I’ve been on so many bad dates that my expectations was really low. More surprisingly are when the dates are good there is still very little follow through. How would things be different if pussy was involved?  There was the guy whose name I can’t remember who keeps sending me dick pics.  We met briefly before the holidays.  We were to meet for coffee, but I was running late and instead ran into his job for a hello.  As the manager of a store right before Christmas things were popping there was a drunk laying on the floor in front of his office with ankles the size of honeydew melons, and he handled that along with all of his employee elves with solid reserves.  We chatted between emergencies and I was delighted that I felt a little tingle (beginning to wonder what was wrong with me).

We agree to meet up after the holidays, but without a provocation he started sending me cock shots saying he was thinking about my yummy ass. At first it was surprising, and also flattering, but, I began to see a pattern.  All directions lead to my ass and his hard dick.  I was unsuccessful when I tried to expand the conversation and neither of them found a time to actually meet.

In fact my experiences may have been the inspiration for why I changed my profile to read, “I want the cock, but also the brains and the heart.”  My last walk on the levee date suggested I update my photos (which are all within the last couple of months…. thanks, pal) and not mention sex. Not that I asked for his advice. If a woman talks about sex that means she wants to fuck anything and everything? Seriously? I wrote him back and told him my photos were recent and asked him this question and he instantly “unmatched me.”  This guy was a scientist and in AA.  I would have expected slightly better manners from him.  Note to self: don’t offer “friendly suggestions” to anyone unless they ask.

Mr. Cock and Mr. Dom seem to be all about THEIR fantasy and exhibitionism.  Where do I fit in? And what was naughty at first became rigid and lopsided.  How is this all that different from the cum and fall asleep program?  When their dick is hard you have their attention, but when else?  Maybe I should find myself a cuckold, because when I have the key to the cage, that motherfucker isn’t going to forget to pick up the milk, no sir.

I’m tired of the mono-syllabic, cavemen definition of masculine and how if I even mention SEX in my profile (DESPITE SAYING I’M NOT INTO CASUAL SEX) that gives the wrong impression.  I can’t be sexual without being a slut and, on the other hand,  I can’t get a men’s attention since I’m way over 25.  What good am I!?  I don’t always want the cock show or to sit in the audience. What if I want to put on my own show?  Can we have a new definition of femininity and women’s sexuality?  Is it STILL true if a woman expresses her sexuality she’s “asking for it.”   Like a short skirt says, “rape me.”  A more erotic profile means I’m cheap and when they meet a real person they are expecting what exactly?

Anyway, Mr. Cock, Mr. Dom and Mr. AA aren’t for me.

So let me tell you more about Gregg. Sorry if I got carried away. He was leaning against a post when I first spotted him–tall and lean just how I like them. Sorry, if that sounds like I’m objectifying him, but I think he would like that.  He was dressed in a sport coat a little more formal than I was expecting.  I was wearing my simple go to black pants and a gauzy, see-though top (yes, I had a black camisole under it) and I liked him instantly.

What I remember more than what he said was this presence.  He had this kindness about him which could be mistaken for a “good guy.” But over the course of the a few hours I saw his range.  Like the Madonna-whore dichotomy, he was both the bad boy with a little bit of sexy edge, but also attentive, open and intimate.  At one point on the dance floor he asked if he could kiss me. A good boy for asking and a bad boy for not giving a shit if we made out on a dance floor surrounded by people.


The kiss was super sexy.  It’s like it encompassed the full spectrum:  soft and sexy, curious and slightly mischievous–exploring my lips and tongue and also urgent and lusty. I can feel it in my body now. Gregg, without realizing it, helped me get in touch with what I wanted because he didn’t overpower me with his agenda. More dancing and bar hoping and then he said, “I want to make love to you.” or was it “Will you make love to me?”

I didn’t answer, now my brain, as you may recall, is my warden. I knew she was going to show up and she didn’t fail. That bitch has some ears. And despite knowing he was leaving at that moment I wanted to make love to him and it wouldn’t have been an “obligation fuck” or a “be nice fuck.”

He asked me as we were walking back to my car why I was hesitant–we clearly were digging each other. And I told him the truth that I wasn’t sure if I could make love and let go and I had a little problem with that in my past. I knew about my powerful tentacles and how I used them to hold on too tight.

Could I open up and knowing it was going to end? Could I allow myself pleasure without creating a shit ton of anxiety for myself? I was carrying this anxiety (particularly because my brother died from AIDS), but I had told myself in a LTR, I wouldn’t have to deal with that, but when my ex had unprotected sex with his new girlfriend and didn’t tell me, it brought up the feeling of never being safe.

Love/sex is risky no matter what…. so was I willing to take the risk?  I finally had gone and gotten myself tested after learning about my ex’s affair and he wasn’t just having sex with Pat, there was a FWB in Canada.

I really didn’t know how to address my anxiety and at the same time allow myself to be present in the moment and Gregg was inviting me to open my body, mind and heart and I was excited, relieved, scared and hot.

I asked him if he was afraid of making love, but he had his mistress waiting (an international and exciting career).  I had to clean piss off the floor, more caretaking and energy draining work. Did it matter that I had more to lose?  No distractions.  Maybe this would allow me to see if I had learned anything about making love opening to a brilliant few hours with another body and soul and then to release them and myself without any linger tentacles? Of course, I would feel the loss, but was that a reason not to open your heart and spread your legs in anticipation of that loss?  Was I strong enough, clear enough to say, yes?  Gregg was perfectly impossible.

Why should I be so careful that I suck the juice out of everything?  I think Gregg reminded me of this when I told him as we headed to my car, “my car is a mess” and he suggested not to think too much.  I knew from dating Henry (the guy I did the clothed massage with, that you can be so careful as to suffocate something.

Gregg was looking for an honest connection clearly it was more than getting in my pants, but he also had that sexy edge and boldly clear that he wanted in my pants. The good boy was talking to the bad boy and I really liked that. Stay tuned we are going out tomorrow.

One thing about my busy online dating life that really helps is there is always a new crop coming up. The other two dates were fun, but the first one the guy was overweight and there was no mention of that on his profile. He was really into me so now I have the job of feeling I have to manage his disappointment. The other guy I felt like I was in a therapy session.  He talked about losing his parents to an auto accident when he was 9 years old and the trauma he experienced with his abusive girlfriend.  I was ready to write him off (and may still) and again feeling the weight of how to do that in the least hurtful way, but he surprised me with his recent text.  So maybe another date, but not tomorrow. That night is reserved for Gregg. Yeah!

And, since I’m a dating slut two more dates on the horizon that I’m excited about and y’all know I’ll be keeping you posted.