Kinda got myself into a bind:

I frequent the same restaurant often and have grown fond of the cutest waitress! Without even thinking, I casually asked her to go out and she (to my shocking surprise) quickly responded "Yes, that would be fun!"... So we are going to dinner Saturday night!!!
 
PROBLEMO:

I am 49yo and she is 28yo. I have known her age for a while and honestly never planned to actually ask her out; it just kinda happened....
 
Should I lie about my age in hopes of stringing her along long enough to get a chance at tapping it and then play dumb if/when the truth comes out OR discuss it early in our date in hopes that she actually might not mind the age difference.
 
Tim

Gainesville, FL

 

From Bob:

 

Tim - I want to say up front, I do not think you should lie. It will bring bad Juju your way and you may end up liking this girl and you do not want to "f" it up over something stupid. Most importantly you may want to eat in your favorite spot again.  If you mess this date up, your screwed at lunch time. 

With that said she most likely knows you are not her age and she is interested enough to test the waters. I would go with it and if she does not bring it up, do not worry about it.   She has seen you chowing down and still wants to go out with you, so go forth on your quest to hit that, with integrity.

Congrats on getting the date with the young lady. You still got it!

 

I would also suggest using "tapping it" as  inner voice phrase and maybe translating it to the public like,  "Spank da.... on second thought considering the intent of the though "tapping it" is spot on.  

 

Good Luck,

 

Bob

 

From Jen:

 

Ohhhhhh Tim, first I have to say "tap it"???? Your 49 dude, come on now!! ;) She absolutely knows you are considerably older than her and it doesn't seem to bother her or she could have easily come up with a lame excuse, as I am sure she gets asked out all the time at work. As a woman in my mid 30's who is around men all the time at work, we can tell a mans age pretty easily. If she wants to go out with you then she probably is tired of guys around her age and wants to be with a more mature established kind of man. So I don't suggest using anykind of terminology like that around her. I'm sure she can talk the smack as good as the rest of us, but I gurantee she gets that kinda stuff from guys her own age and there is a reason she wants to go out with someone older. She will ask you if its a big deal to her exactly how old you, so for the love of God don't lie about it. You have no idea where this could go so don't jack it up from the get go.

Next, as I woman of course I get why you want to "tap that". And frankly, women are very much like men we just don't usually come straight out and say that. So, she may want the same thing you just never know. My suggestion is take her lead with this one. Be respectful and she what happens, if you get the goods then good for you AND her!!! Where it goes from there nobody knows. But, if you want it to go past just sex one time, then the key is to treat her like a lady and that will get you the best result. If all you get is a fun time at dinner, that's great. If you get to "tap it", then score!!! Its all in your hands Tim, be smart about it and ya never know what can happen.

Jen

Comments

[Leslie]

wow... this guy sounds like a real winner. He'll be lucky to tap or spank.