This is probably the first close I've done in about... 4 years?
My biggest stick is the initial approach, and while in this set I didn't actually approach, I stepped way out of what's normally comfortable.
Alright, so I got on my plane heading back home, and ended up sitting next to this girl who I'd say was about a 7. I asked if I could switch seats with her so I could have the window and she agreed. I did that for two reasons: I'm a pretty big guy, and a lot of people find me intimidating, so I figured her sitting in the aisle seat would make her feel less trapped. I also did it because if I should totally flop, I could use the wall to rest my head and go to sleep.
I opened by asking where she was heading, and she said she was going home (cool, she lives near me). Naturally I asked what she was coming home from (judging by her appearance, something to do with business), and we got to talking about her work.
She asked what I did, and I used the disposable lighter repairman line. Now, I've used that one before and 95% of the time, I at least get a smile. She kept a totally straight face and started to ask particulars about my line of work. Totally unprepared for that, I lost it and laughed, so did she. At which point I told her what I really did, but didn't go into detail too much.
So I told a few jokes, sneaked in a few negs, and did a couple of magic tricks (NOT easy on a plane when you've just started learning magic). I felt like the small-talk was starting to go nowhere, and the lulls in conversation were getting longer, so I shifted gears.
I asked her to give me her hand, and she asked why. "I also happen to be a psychic in training," I told her. She began to reach up with her left hand, but quickly switched to her right... not before I caught a glimps of something shiny where I didn't want to.
She was married. However, she didn't once in our conversation about her moving to the area, her job, her kids, not once did she mention a husband.
I took her hand in mind and squeezed a little, and she responded in kind. I went into some cold reading items that I was reading up on, and with each one, her smile grew bigger. The last item I touched on was, "I sense that you've very recently lost someone. Not necessarily due to death, but someone important is no longer a part of your life." She was smiling ear to ear, and I could've sworn that her eyes were glazing over.
As we were landing (it was a short flight, 40 minutes), I handed her my cell phone and she put in her number. When she got up to get her carry on from the overhead, I noticed that the shiny thing on her left ring finger, was no longer on that finger.
I didn't stick around after that, or walk with her. Rather, I walked ahead. Though I did say bye to her, and made her give me a kiss on the cheek. She was still smiling when I left.
I know that closing a 7 isn't a big deal, and that I didn't overcome my sticking point, but it was still a huge confidence boost.
What things did I do right? What could I have done better? And why don't I feel bad about messing with a married woman?