Uptown Rantz

Don't Wanna Be No Uptown Fool

Archive for the category “My Affair w/ Married Allison”

“My Sinful Thoughts”


This was one of the first e-mails we exchanged through our personal, non-work e-mail accounts, and I guess it led to everything that eventually happened. Prior to this, she was just a cute, married friend at work who smiled every time she saw me. Then in this e-mail she tells me that she’s attracted to me.

In one of the previous e-mails, I suggested getting together at a cool bar near her house for a drink sometime. She replied that it would not be a good idea for her, and I thought it was because she didn’t drink. She clarified the reason in this response. And I didn’t think it was weird that she Googled me or checked out my MySpace page (remember those?). I was quite flattered, in fact.

It did strike me, however, that she told me she was attracted to me in this e-mail. To tell me I’m attractive would have been one thing, but for her to say she’s attracted to me and that something might happen if we went out for drinks was another thing entirely. Her marriage was just over 1-year old at this point, and this e-mail completely altered the way we related to each other.

Being the other man in an extra-marital affair was not something I anticipated ever happening to me – not even close. But the door was now open and I walked right through it.


“I Pissed His Trust Away Today”

* e-mail from Allison – click to view larger (I redacted her husband’s name)


The image is an e-mail Allison sent me right after our first heavy make-out session. That make-out ended-up being the gateway to our affair.

We were embroiled in a marital affair typical of a Lifetime Movie of the Week starring Judith Light. Allison was married, so for her it was an extra-marital affair. For me, it was just a single guy doing things you shouldn’t do with a married woman.

I took notice of her right away on her first day of work…a cute brown-haired woman with an even cuter little body. I also saw the wedding ring. The work e-mails during the day turned into e-mails on our personal Yahoo accounts at night. The coffee breaks at work turned into coffee at Plan B in Uptown and beers at the Turf Club.

We went to movies (held hands at Juno), talked late nights on the phone (her talking from her basement away from her husband), had pet names (I called her “hun,”she called me “sweets”), went to dinners (she didn’t have a joint checking account so she paid sometimes) and logged quality time on my old red futon couch (she felt amazing in and out of her sweaters).

She fell in love with me…the e-mails, cards and old-school love letters she would give me at work went on and on about her falling in love with me, and falling out of love with her husband. I wasn’t in a relationship at that time and more than a little lonely. I had this adorable woman throwing all her love at me, emotionally and physically, and it was hard to turn it away.

I felt momentary stabs of guilt when I would catch myself thinking that my girlfriend is married and it didn’t seem weird. The absurdity of it all would hit me and I would pull back my emotions from it. Then she would come over to my apartment on Humboldt, smile at me, take off her shirt before the door was even closed behind her and the guilt was gone – replaced by that tight little dancer’s body on top of mine.

She would arrive home from my place late and her husband would already be asleep. Lying there in fear that her husband would smell another man on her – a late night shower would be too suspicious – she would cry convinced she’s married to the wrong person.

But there’s periods that all people go through when they think they’ll never be loved. This past winter was one of those periods for me, and knowing Amanda was engaged made it even worse. I would read Allison’s love letters over and over while the snow piled up against my windows and the wine piled up in my liver. Her letters helped.

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