Trick or trick?

Halloween is just around the corner and so are the children in customs and parents buying candy.  Many of my friends who have children are super busy preparing and I’ve never been thrilled about it. I am the one who turn off the lights to avoid the tricker-treaters come over begging candy. 

Amongst the people at the store buying candy is Jack, a guy I hooked up with around Halloween of last year. Jack is in his mid 40s who lives in my neighborhood. We chatted up on Skruff many years ago and decided to meet up one night. Turns out he is married (to a man) and they adopted 2 children. Like every other couple, they were in an open relationship. He explained “It works very very well. We are totally open and honest with one another and to be honest I think it spices things up for our relationship as well.” They have played together but mostly separately. Which is what Jack and I did. 

Jack invited to me his house. His husband and children were staying at a temporary place while their kitchen is being renovated. Despite their “openess”, I was nervous and still felt like I was doing something unkind. My friends joke that I am a home-wrecker for constantly hooking up or flirting with guys in relationships, but they have mostly been in open relationships…. or least that I know of. Read about my first and only threesome experience, 3-3, and Keegan Singled Out.

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awkward first date

About 5 years ago, I was at a bar and saw this guy who looked like an older version of Justin Timberlake. I walked up to him to confirm if he was actually Justin Timberlake. He was very flattered to hear this. 

arrives at the world premiere of Twentieth Century Fox And New Regency's film

His name is Harry, not Justin, who is about 5 years older than me, white, super tall, dark hair, and has a Long Island’ish accent that was almost intimidating.

We met up for coffee next day. The interaction was so different from the exciting conversation we had at the bar. We talked about 3 top things you should never talk about on a first date: religion, politics, and ex-boyfriends. After we talked about those,  we ran out things to talk about. There were many long awkward silences… about 10 minutes of it. 


To bring sexyback, I try to give everyone a second chance if first date didn’t go well. We went to a swanky bar and had a bottle of wine. I was hoping he would be more relaxed with some wine. This time not only he was boring, but he seemed to have a bitter attitude. It’s too bad, because I really like Justin Timberlake. 


See The Guyliner’s blog about first date: 33 lies you will tell yourself on a first date.