[Vincent Chase]

Have a couple of dates set up for a hotel bar. Can walk around with them outside a little first say to a park a bit first then go to a bar in a hotel to make it appear more as an adventure than just a sit down at a bar. I can't take back to my place at the moment.

The logistics for this appear to be more complex. Paying for the hotel room before the date (say 100 dollars) could be a bit of an expensive waste as nothing is guaranteed.

What do you guys suggest is the best way to transition from a hotel bar to a hotel room upstairs?

I have done this in the past but only on second dates (and screened for likelihood of sex). But I don't want to throw money on first date with low chance of success.

As we all know it needs to be as natural as possible. Do I set up expedia ready on my phone for the possibility and open it up quickly if it's going really well and book it there and then and quickly get the keys?

[Dr. Howard]

Don't use the hotel bar, use your hotel room as a venue change from another location. Also, suck it up and pay for the hotel room beforehand. It will make you push for the close seeing as you are already invested.

[MrXY]

I don't like the idea of meeting at a hotel bar for a first date; it's too likely to activate her anti-slut defense. I have banged plenty of girls on first or second dates or girls I picked up that night at hotels, but I didn't meet them there. They are too likely to get suspicious and defensive if you go in cold to a hotel.

There are two ways you can handle this. Meet her at a venue within walking distance. If things are going well, bounce to a couple of other places. After a few drinks at these places, suggest going to the "cool bar" at the hotel. It's better if this is a bar or restaurant that is a happening place that attracts non-hotel guests as well. After hanging out there for a while, tell her you don't want to drive home after drinking and are going to get a room. Don't invite her up at that point. Get the room and then ask her if she wants to come up for a drink before she leaves. Everything "just happened" , right?

The other way is to get the room in advance, then do the multiple bounce thing, then tell her you were worried about driving so you got a room. Mention a friend who got arrested for DUI and how much trouble that caused him. Tell her this before you go to the hotel bar; better not to spring this on her when you're already at the hotel. Just tell her to walk with you back to your hotel and have a drink in the bar before she goes.

If you're going to put up the money for this in advance, have a backup plan in mind. If you're not vibing with the girl during the bouncing and if your screening detects that she's not DTF, just bail out. Then go with Plan B, which should be going to other nightspots nearby and cold approaching. Hit your own hotel bar at least a couple of times that night; some hotel bars are great places to pick up ONS girls. Have a story ready about why you're staying at the hotel-business travel is a good one.