To be fair to both myself and the young lady I would prefer some time first to test our compatibility.
Plus you also need to factor in the cost vs. benefit of spending so much time with a complete stranger as opposed to shorter dates with several other ladies.  
My personal preference would be an introductory date of ~ 1.5 - 2 hours. If all goes well then for a second date I would consider ~4-5 hrs. for dinner. Then perhaps for a third date it could be an overnight if by then I consider her my "regular/favorite." For me, an overnight is something that I would only do with a "favorite" lady.

nycad

You state you have 2 overnights, but they can cancel at anytime, so it is not a sure thing.

and those who  tell me  author and what is novel about (in private PM ) will have my overnight  as  for 3 hours  roses .. yours .. Madam Patricia you made my day !!
Kisses to all inspiring  with business they are in...   and ladies and gentlemen

Amen (e)

I personally think overnights are fun. Ive done plently of first time meeting a hobbyist in an overnight. I will say its not for everyone and I do believe in doing your research on a girl to makes sure her reviews are up to standard. I do have one client that I met him for the first time in an overnight and our appointments in the future became overnights. We even had two separate weekend trips out of town, one being in Austin, TX and the other a wine trip out to CA. He was fairly young so it made it fun to go out to dinner and have drinks. We still communicate til this day through email.  

It seems that NY men like to develop a relationship and more chemistry before committing to something like an overnight and, unless they are single, it's pretty impossible for them to have dinner dates and overnights. 95% of my NYC overnights are out of town travelers.

I would be more amenable to an overnight stay as well. I was away from home, no worries, the company paid for my room (as well as dinner with the lady), etc. I had an ATF in a city I used to visit ~ twice a month and I would do an overnight with her each visit. But again, our first date was not an overnight - once I saw a "connection" then she became my regular for that city.

Gentleman talks to me let say a month ahead ... it is not as same day overnight .. yes  it never take place and I never take same day request for overnight ,, you know feels wrong you never know .. but I  found myself quite often  with overnight with men I never met before  we just  talked over email did share what  we do who we are ..  and we pretty well already know each other  so there is not worry .. and it can be different kind of scenarios ..... normally I meet him  in the bar .. sometime he tells me that room will be opena nd I have to enter ..and nobody be there ..just chocolate on bed and  champagne in ice .. then I take off my clothe myself and  laying dow on bed .. him to come .. we make fast  first time not talking ..  then we  take shower dress .. and if we have time drink a  bit ..if not  if there no time  for concert or show I booked or him  - we rushing to   clubs . ( always then he surprised how do i know such nice places.. and I surprise that you gentlemen even form NYC that you do not now : so I am always gald to share ..)
 so we come bacl around  11 or 11 30  pm  back to room .. and here   all depends or we are so horny so just making love till we  all totally wasted .. or we first talking kissing and foing a lot of calm intimate staff .. sometime we talk a lot .. sometime I share my  musics my culture then he shares his presentations what he does ..and why he is NYC .... we drink and running naked in the  suite F**Ing  and   talking  
 then we just fall in sleep ..  and sometime I found myself taken again in the morning .. sometime not .. and it depeneds if we have lunch .,,
if I have few days .. let say Vegas .. we  just  sleep till let say 12 pm  then wake up going to eat .. then come to room  make sex again .. take shower go to spa or just to sweaming pool till eve .. or he goes alone gamble I am not .. or just walk here and there .. come back to room making love .. get ready to eve  show  nigth club or strip club ..ine day can be show next day dance club... and  !!! O Boy .. I love men who take let say 3- 5 bottle of vodka vine .. etc .. so everybody around us drinks with us and it is soo much fan .. attract people  in the bar  smart men knows .. if he put drinks and  those be free there be a lot of  youth around  and boys and girls and we dance  and they dance and we are all freins and time just ..  fan fan fan ..  and  day like that . and next day .. let say strip club .. but there  you know . just watch . for lap dance in private room no more then lap dance .. it is about 1000 ... so my men take me there only if I want .. when I never was there I asked  invite other  girl .. now I do know that other girl in strip club..  would not  be FS and more likely even would not let touch her hair .. of of course cub is good but will charge 1000 so ..  I not take my men anymore there .. becuase it is too much $$$$ and .. now I know all  that staff .. but before .. if he asked me if I want other woman ..I say - yes ..  was curious ..  
 you know there a lot of staff to do  ..
 and it doesnot matter if we met before or not .. it is abotu connection ..
 you know I share more .. before when I was trying just to date  not as escorting average men told me - let s meet in Starback and see if there is connection .. and I tell him - there be NOT connection from me in Starbuck first date
invite me to nice place with bottle of  nice champagne ..  it be .. connection on the spot ..:
 and you  .. here   those who in hobby tell - never overnight on first time !!! :Lovers !!!of  course I do not tell that I would not do over if we meet first time for 2 hours only .. but if you insist and keep be telling  - I will do only second time .. hmm...
 I possibly would skip it .. second time .. there be  and two hours .. too  much  to be bored ..
 those who ready take over just  from talking to me ..  those .. those  be lucky once .. and I not afraid travel  to out of the state  to overnight .. my first one .. was when I was in CO and  he flew me to CT .. again please know - all what you need know about  woman - it is communication !!! not nessry to be with her .. of course given you see nice women  .. safe  .. and well reviewed ( when I said well I not meant 150 + reviews ..) so let  s do it  may be ..  
 and I mean  
 start talk to me Lover .