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Last night I went out on my second date with Anna, the woman I picked up at the bookstore a few weeks ago. It was kind of a disappointing date after the first date went relatively well.

My main issue with her is that she’s a constant talker. I wouldn’t necessarily mind – my friend Yvonne also tends to talk a lot but it’s different with her. Anna just seemed to talk and talk and talk only about herself. She never asked me any questions about my life or my interests. I felt like I had to jump in and tell her about myself in the short gaps of silence that she would take in between her non-stop talking.

Here’s a tip for you women out there – ask the guy questions, too. I happen to think I’m a pretty good conversationalist and I take an active interest in the people I’m hanging out with. But I expect SOME reciprocal interest from other people. This wasn’t the case with her. Maybe she was too nervous to ask me anything or didn’t know what to ask, but I just found it boring to sit there for 2 hours (the length of our date) and listen to her go on and on about her life and her interests without feeling like she cared about mine.

I have to say – I’m a sucker for women that ask me about my interests, my passions, my beliefs, etc. I feel I do that with women I go out with but I don’t often get it in return.

My second issue is that I’m just not that attracted to her. I sensed it when we first met at the bookstore but I thought I shouldn’t judge her so quickly. But after going out with her twice now, I think it’s an issue for me. If you must know the details, she’s overweight. Not like Angela but enough that I notice. She’s got thicker arms than I’m used to seeing on a woman and her body is just not the type that really turns me on.

During our date I noticed a really hot woman come in to the restaurant and sit at a table less than 10 feet away from me and in my line of sight. She was there by herself and no one showed up to join her while she had an entire meal. She was obviously lonely since she checked her cell phone a few times during her meal and I couldn’t help but feel this surge of confidence that if I weren’t sitting with Anna (and getting kind of bored) I’d totally approach her. I was most fascinated by the fact that I didn’t experience any approach anxiety. I just thought – hey, I made this challenge for myself, I’m currently out $50, I’ve been practicing talking to women already, I’m feeling attractive and confident and this could be a lot of fun! I think that was my favorite part of the evening – fantasizing how I would approach this hot woman.

My third issue with her is that she’s a judgmental condescending perfectionist. For example, she’s a big connoisseur of food and takes a lot of pride in her cooking abilities. That’s great – I love it when people have interests they’re passionate about. But she seemed to cast judgement on me when I recounted how I cooked a dish. As I’m telling her my story she got this condescending look that told me she thought I was doing it all wrong. And the way she spoke to me as I was telling her my story – like she was trying to suppress herself from saying, “You’re doing it all wrong”. Man, that’s a big turn off.

She also told me she’s not a very patient person in the kitchen with others and told me a story of how a friend that didn’t know how to cook was helping her out but she lost all patience with him when she realized he didn’t know the difference between dicing and slicing. She ended up making the entire dish herself while he passively watched from the sides. I just thought, “You’re someone that prefers to be right all the time versus seeing opportunities to connect and share yourself with others.”

Now, I happen to be into running and if someone totally new has questions or is doing something I disagree with, I would look at it as an opportunity to have a meaningful conversation where I share with them my experiences and ask them questions to understand them better. I wouldn’t act like they’re a moron and I’m this expert.

So after a couple hours of this, I thought I should cut my losses and suggest that we get going. I paid the bill just like I did the first time we went out. She offered to contribute, but in that half-hearted way that made me think it was more of a polite gesture than a real offer. I just shrugged and said it’s OK. Maybe I should’ve split it with her after all – not like I was planning on seeing her again and this wasn’t our first date. Then again, we just had a couple of drinks so it wasn’t like we had this full meal. I think taking a woman out to dinner at a restaurant is total overkill for a first, second, or even a third date. Too much pressure, too expensive (if you plan on dating multiple women) and it doesn’t contribute to the fun factor.

As we were walking out of the bar, I noticed this attractive woman talking with a guy by the window. As I was walking towards the exit, the woman and I exchanged a glance. I felt she was checking me out and I held her glance – whereas in the past I would have been likely to turn away.

I offered to give Anna a lift to her place but she preferred to walk. I ended the date by hugging her and telling her I had a nice time (that’s the nice guy side of me not wanting to hurt her feelings). She didn’t insist on a date for our next date, so maybe she felt the spark wasn’t there, too. She said, “So we’ll call each other to go out again.” Maybe she was going through the motions, too. I kind of kicked myself for not being more upfront and honest with her right there. Now, I’ll have to make “the phone call” to tell her what I could have said last night. I think I just didn’t want to hurt her feelings, in case she thought we had this great time. After all, she got to talk a lot and express herself. I guess I didn’t want to splash cold water on her face and tell her that I’m just not into her right at the end of our date. I wanted her to think that I spent some time contemplating it before making my decision – that’s the nice guy side of me that’s trying to please women and not hurt their feelings coming out.

I think it would be OK to stop seeing Anna – if the spark isn’t there there’s no point acting desperate and continue seeing her “just in case” things improve or I won’t manage to find someone. I can already feel how knowing I can easily go out and meet more women keeps me from compromising my standards. I can’t wait to complete my approaching women challenge! It’s working already!

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