Yesterday I went out to dinner with my family. There were 5 of us – my parents, my sister, her boyfriend and moi. We went to a relatively nice and trendy place – my sister was taking us all out to celebrate her job promotion.

I hadn’t really planned on practicing any pick ups, especially with my parents around – but I found that that side of me just naturally came out – I wasn’t even trying. At first, there was another group of diners sitting at a table across from us – a family with 2 grown daughters and a son. It just so happened that they were in my view and I exchanged a couple of glances with one of the daughters.

Then there was our waitress – attractive, friendly and open (not cynical and just “going through the motions” like many waitresses do).

I’ve never tried picking someone up at a restaurant before and I found it a relatively easy experience. The waitress had to come by our table multiple times throughout the evening and those were great opportunities to exchange a few words and have these mini conversations and build a connection with her. She came by with a bottle of wine and my sister was the one who was supposed to approve it – so I asked the waitress if anyone had ever sent a bottle back which turned into this nice exchange between us. Or the time I came back from the bathroom and the waitress had asked me if I wanted to order coffee like everyone else had and I joked with her that that was a lot of peer pressure but that I was going to be different and order tea – and we had this little exchange and shared a couple of glances during that.

My family was apparently noticing my behavior and at one time my sister made a comment that I was embarrassing her, which I thought was strange. I was just talking with the waitress a bit more than most customers do but I wasn’t doing anything inappropriate. I don’t think my mom, dad or my sister’s boyfriend minded. I just think they were used to seeing me behave a certain way – since I wouldn’t normally flirt with waitresses and this was a bit of an eye opener for them. They don’t know anything about my pick up practice so this was their first glimpse into my new way of life.

I decided I was going to ask out our waitress somewhere towards the end of the dinner. It was one of those decisions that I didn’t hesitate on – I really wanted to do it – no doubt in my mind, no nervousness, just a determination to do it. I felt I had a connection with her and that I’d feel better for doing it.

So I had to wait for the right time – I didn’t want to do it in front of my family so I waited till we all started getting up from out table and I told them I’d go use the bathroom. My plan was to ask her out while they were waiting outside by the car. But then my mom said she needed to go to the bathroom, too. Damn! I didn’t want my mom seeing me ask out the waitress (not that that would have been a big deal). Everyone else waited at the front of the restaurant for us.

I went into the bathroom and quickly came out, thinking that I could do the deed while my mom was in the bathroom. But I couldn’t find her! So I asked one of the other waitresses to find her for me. She soon appeared and had this look like “Is everything OK?” Maybe she thought I was going to make a complaint or something.

I told her in a relaxed manner with a smile on my face, “Listen, I don’t usually do this, but you seem like a really genuine and nice person and I was wondering if we could go out sometime.” She smiled and said, “I think my boyfriend would have a problem with that.” I replied with, “Well, he’s a lucky guy.” and was ready to leave and then she added, “But if you come back we can have a drink at the bar.” I said, “Sure, that sounds nice” and went to join my family who were still waiting for my mom.

Things I Learned

  • I felt really good about asking her out – I wanted to do it no matter what her response would be. I’ve noticed this many times before – the fact that I show my interest in a woman is more important than her response. This might evolve over time but I’m still feeling like I’m learning how to connect with attractive women on a consistent basis, so it’s more important to keep trying and experimenting than any one individual result.
  • Having her see me with my family automatically gave me credibility and made her feel safe – I’m not some guy that approached her on the street. Instead, she could see that I’m out with my family and that I’m a normal person. I think this could be used in other situations – like going out to meet people with a female friend, so other women can see that I have women friends.
  • I worked on the connection little by little, each time she came by our table. I would ask her some question about the menu or the way she did things and it was an easy conversation starter. That way, I could see whether I liked her personality and there was a basis for me to ask her out later. Just because a woman is attractive doesn’t automatically mean I want to go out with her.