This past weekend I was on my way to lunch with a coworker while on a business trip. When we arrived I noticed a hot waitress in her early twenties with dirty blonde hair and a great body in the restaurant. I silently brought her to my cw's attention and gave him that look that says, "It's on!"
We were seated in her section and ordered drinks casually. IMO, waitresses have been an Acilles heel of mine. My conversion rate into anything positive is lower than almost any other profession/situational setting that I've encountered. Lately, I've been using a mix of being quiet most of the time with some playful flirting at the right moments(better results lately) which is how I was approaching this.
The co-worker of mine, who I manage, winged me like a champ subtlety letting it slide that I was the boss. This came across as sincere because it was the truth and he's much older than me (early 50's). I played it off and turned it into a joke between her and I.
We were there for awile, it was a lazy sunday plus my cw had a cold and was ordering bowls of hot soup and whiskey. The waitress and I were ordering different drinks for him and having a good time.
My cw split at the end of the meal to give me time to pay and talk to the waitress. She brought the bill, we flirted, and I asked if she was single to which she replied yes. I asked her out and what her availability for the next couple of days was and she immediately said Friday, took it back then said Monday night(the next day). I agreed and she put her number in my phone. I paid, left a good tip and got outta there.
A few hours later I texted her a standard ping message dropping my name in case she forgot. She replied positively and in a reasonable amount of time.
The next day I get a text from her after lunch. The standard "Hey!" bullshit. I hate this text, I think the correct reply is "?". Gonna try it next time I get that one. What do you guys think?
I was at work and said I'd text her when I was done. She asked about my job and I gave a positive, short, general statement about it
When I texted her that evening about getting together she replied back, "What are we gonna do?" This text always trips me up and I feel I never get it right. Feedback on this would be much appreciated.
I text her that I wanted to meet up for some pool and the usual get to know you stuff. She agrees and asks to be picked up bc her car has out of state license plates and she doesn't want to be an easy target leaving a bar. I agree,(its 5 minutes out of my way) and she texts me her address.
I leave to pick her up and when I'm three blocks from her place I get a text that she's not gonn make it and to have fun. Flakes are common but this last minute one kind of irritated me.
I texted back no big deal maybe some other time. She instantly replies that some other time would be "okay". We haven't texted since that night and I'm conflicted about whether to try agin. I'd like to hear what everyone thinks.
Thanks, Rocco
We were seated in her section and ordered drinks casually. IMO, waitresses have been an Acilles heel of mine. My conversion rate into anything positive is lower than almost any other profession/situational setting that I've encountered. Lately, I've been using a mix of being quiet most of the time with some playful flirting at the right moments(better results lately) which is how I was approaching this.
The co-worker of mine, who I manage, winged me like a champ subtlety letting it slide that I was the boss. This came across as sincere because it was the truth and he's much older than me (early 50's). I played it off and turned it into a joke between her and I.
We were there for awile, it was a lazy sunday plus my cw had a cold and was ordering bowls of hot soup and whiskey. The waitress and I were ordering different drinks for him and having a good time.
My cw split at the end of the meal to give me time to pay and talk to the waitress. She brought the bill, we flirted, and I asked if she was single to which she replied yes. I asked her out and what her availability for the next couple of days was and she immediately said Friday, took it back then said Monday night(the next day). I agreed and she put her number in my phone. I paid, left a good tip and got outta there.
A few hours later I texted her a standard ping message dropping my name in case she forgot. She replied positively and in a reasonable amount of time.
The next day I get a text from her after lunch. The standard "Hey!" bullshit. I hate this text, I think the correct reply is "?". Gonna try it next time I get that one. What do you guys think?
I was at work and said I'd text her when I was done. She asked about my job and I gave a positive, short, general statement about it
When I texted her that evening about getting together she replied back, "What are we gonna do?" This text always trips me up and I feel I never get it right. Feedback on this would be much appreciated.
I text her that I wanted to meet up for some pool and the usual get to know you stuff. She agrees and asks to be picked up bc her car has out of state license plates and she doesn't want to be an easy target leaving a bar. I agree,(its 5 minutes out of my way) and she texts me her address.
I leave to pick her up and when I'm three blocks from her place I get a text that she's not gonn make it and to have fun. Flakes are common but this last minute one kind of irritated me.
I texted back no big deal maybe some other time. She instantly replies that some other time would be "okay". We haven't texted since that night and I'm conflicted about whether to try agin. I'd like to hear what everyone thinks.
Thanks, Rocco
