Meet Me Halfway, right at the Borderline


As my stylist applies the dye to my progressively grey roots, we start chit chatting about plans for Saturday night.  I’m excited to tell her I’m having my 8th date with Joe. 34. Egyptian. Healthcare Compliance Manager. Jersey Homeowner. 6’ Beefcake.

Ironically, this is my least favorite weekend of every single month because it’s the one MSP stays with the Chupacabra of Joy. So when I don’t have her, I like to keep busy; ergo getting my hair done at the salon.  It’s not an avoidance of being alone; I love alone time.  I stay busy, so I don’t miss her…so, I try to catch up on chores, bills and go out with friends; plus an occasional worthwhile date. Keyword: worthwhile! Considering the last date I shared, you can understand my attempt to be more selective.

So, since Joe and I were seven AMAZING dates deep, I figured it would be safe to offer him my ONE free Saturday night to hang out.  At the time I mentioned it, Joe was planning a trip to Miami, so it wasn’t going to work out.  But then, the Monday before the weekend he told me that his trip fell through, and asked what I was doing…since I hadn’t made any plans, I offered to hang that night.

But then he says, “Ok great. But I gotta make sure my brother doesn’t need a ride, so let me confirm with him, and I’ll let you know for sure…”

“Okay, um, Joe, your brother is 24 right? So why do you need to be his Uber?”  He goes on to explain that since his mom is traveling overseas, he’s in charge of his brother to ensure he doesn’t get into trouble and goes to work. He’s like, “I told you, babe, my family is high maintenance.”  I quipped back “More high maintenance than my 8-year-old? If you say so…”

With that my “spidey” senses go up…it’s a bit suspect to me.  But I let it ride, because at some point I need to trust that what people say is true. While these family demands feel a bit sketchy, the fact of the matter is that when we are together, it’s incredible.  He’s attentive, kind, emotive and affectionate.  The conversation flows, and it’s just easy with him; easy like a Sunday morning, kind of easy.  It’s just getting to the fucking date that’s annoying! Add the fact that I’m Italian to my dating track record, I battle paranoia with every single guy I date, particularly with Egyptian Joe.

What you should know is that because of these challenges, I’ve attempted to break things off with Joe several times or as he claims “I tried to leave him.” Not because of anything specific per se but the fact that we are in different life phases and he wants very much to be married and to have a family. I’ve explained to him while marriage isn’t entirely off the table, birthing children is firmly off the table (I would always consider adoption, and if my partner came with kids, that is wonderful).  I’ve been there, done that and got it right the first time. I’m good.

And yet I keep going back to him, because I really like Joe. We have five levels of connection, and that is a fucking straight up record for me!  He’s super-smart, funny and silly. He has this infectious positive energy, and his laugh makes me laugh. He has the kind of smile that makes me feel like I’m under a warm blanket on a cold, snowy day with a glass of wine. He’s driven, family-centric (to a fault), very stylish and adventurous. It’s so stupid, but he LOVES seafood! (Yes, this is a non-starter for me; sharing food is one of my favorite things to do, and seafood is my #1).  He’s also down to earth and direct…and the chemistry is just, electric.

We are, however, missing some of the X factor (right time) so while I’ve been authentically me, I am cautious because we have that major conflict looming that could inhibit any potential for the future.  The ever-present issue with dating for me at 44 years young, is that older men want younger women and younger men are typically cougar hunters.  The younger men I’ve dated are not intimidated by my success or my alpha personality.  In fact, they are intrigued and inspired by it.  Older men, by comparison, want to be more in control and are interestingly more competitive.

This time in my life has awakened me to being present, living in the now since my vision for the future is not very far out.  I’ve achieved everything I ever hoped for and more; and have this incredible blank slate in front of me.  What I am quickly realizing though, by dating younger men, many of them are in a phase of planning for the future.  This is a life phase conundrum that has no specific resolution. It just is.

So, after my third attempt at unsuccessfully breaking things off with Joe, I posed a rhetorical question to Joe (and to myself)… “Let’s say you found your dream sports car (we are both obsessed with sports cars) and you are insanely excited about it. You know that you’ll go on some fantastic road trips and have the time of your life. But you also know you’re going to get into a crash and come out with some broken bones. Do you still get the car?

He quickly responded, “I would just get better insurance.”  Oh, Joe, you clever, clever man. So with that, I laugh and continue to date him.

Interestingly, my good friend’s husband told me once that I need to up my standards; that I need to stop “shopping” for guys at Wal-Mart when I deserve Louis Vuitton.  I took that statement literally at first, and quipped that I don’t even like Louis Vuitton! But after meeting Joe, I finally understand what he meant. My hope fights with the paranoia, so I continue down a path I know has an inevitable ending.

While at the salon, I am still buzzing with excitement about seeing him and going shopping for home décor at Home Goods (Home Goods is my décor porn).  He just recently bought a house, and it needs a lot of design help.  And when I mentioned to him that I started my own Home decorating business, he was excited to work together on fixing his living room!  What better date than to marry two things I adore…shopping for furniture and my sweet Egyptian Joe!

After finishing at the salon, I’m feeling lifted.  Hair looks great, the weather is beautiful, and I’m listening to great music on my ride home to get ready for the date.  My enthusiasm is brought to a screeching halt as I pull into the driveway and see a text from Egyptian Joe…

Egyptian Joe: Babe, I am sorry, but I have an emergency I need to attend to. I’m going to need to take a rain check…I wanted to tell you, that’s why I called.

Cherry: Is everyone ok? Define emergency, so I can decide how disappointed I am.

Egyptian Joe: You’re not the only one disappointed.  The shit literally hit the fan! My father’s septic tank clogged at the house and now my Dad and I need to fix it.

Cherry: You understand I expected this right?

There it is.  Shit happens, but jeez, seems quite odd that he only confirmed plans that morning and then a septic tank blows that afternoon.  Just something suspect about it (paranoia is winning over hope).

We clearly didn’t have the 8th date, and while I try to keep my head up, my disappointment is palpable the rest of the night. It made my heart ache a little. Apparently, my feelings for Egyptian Joe are stronger than I anticipated, so I need to assess whether to buy the car or not…right now, I’m renting.


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