Yesterday I forced myself to get out of the house and interact with at least one woman. I didn’t impose the same rules I used in the approaching 50 women challenge. I’m trying to be more loose and easy on myself, especially since I feel I’m out of practice and need some time getting back into that headspace again.

I was running and spotted a cutie walking towards me. She came out from an adjoining path so it was a bit of surprise. I hesitated and didn’t stop to talk to her. Unlike before, I didn’t beat myself up. I just figured I’d approach another one today. Sure enough, later in the day I had to go grocery shopping and that’s where I got a chance to really exercise my pick up muscles.

Approach #53 – Grocery Store – Woman by the Grapes

I first briefly talked to a lady by the grapes. She wasn’t great looking, just average, but I wanted to interact with at least one woman today. As she was standing by the grapes and looking over them, I just walked up casually next to her and asked her if the grapes were any good. She said they seem to be and then I asked her if she sampled any. She said she hadn’t so then I pretend she was being really bad by saying “I thought EVERYONE samples grapes in stores” and gave her this look like “It’s OK – I won’t tell on you if you do it.” So she went ahead and sampled the grapes and told me they were quite good. That made me feel better – like I was very slowly getting back into the “not caring” mindset I was at before.

Approach #54 – Grocery Store – Hot Customer

While I was standing there, thinking how good I felt, I saw this very attractive woman walk right past me. I just saw her pass me and admired her figure but felt immobilized to go and stop her to talk to her. So I continued walking up and down the aisles, making short conversations/comments with women I’d pass in the store. Then, as I went into the next aisle, I noticed the woman that walked right by me before. She was standing by the tea section and trying to figure out which one to get. Now, I’m not a huge tea drinker and I wasn’t planning on buying any tea. But since she was there, I just made my way towards her and opened with “Which one’s a good one to get for very special guests?” She smiled at me and gave me a few options. We bantered for a couple of minutes about what teas are good to get depending on which types of guests you’re having (pretty silly topic of conversation but it was fun). I noticed she had an accent and I asked her about it. Turns out she’s from the same country I’m from (except I don’t have an accent). She was quite surprised at our commonality and we talked for another minute or so. After a while, I didn’t say any more – not because I was getting nervous – but because I felt I had done what I wanted to do. So eventually she excused herself and continued her shopping. I felt good for just walking up to an attractive woman and starting to talk to her.

Approach #55 – Grocery Store – Cashier

As I was checking out, I made sure to go the cutest cashier I could find. But as I was about to start putting my groceries on the conveyor belt, she said she was closing and directed me to another cashier. I made this mock refusal saying I wouldn’t leave and that she would have to ring me through – she could tell I was joking and we exchanged a nice moment of connection.

I went to the cashier that rang me through and I ended up bantering with her, too! I let this old lady go ahead of me who only had a few groceries and this was a topic of conversation between the cashier and me after the old lady left (the old lady didn’t speak a word of English – luckily both of us spoke her native language). I talked with the cashier about where she grew up, when she immigrated to the country. I even told her that if she was a bit older I would’ve asked her for her phone number. That made her smile and I could tell I probably made her day. As I finished packing my groceries I told her bye and it was like we were friends now.

I’m really beginning to get back in the groove with this. I’m wondering if I should approach one woman a day – not to necessarily ask her out, or even talk for a minute. Just to say something to her – so I can get used to starting conversations with women in public again.

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