You can also bring a lap top (or some business like bag)... As if you're there for a meeting :)

Just make sure you're not carrying flowers and candy with you LOL.  Have fun!!

What attracts attention is standing around. Don't hang around in the parking lot or the lobby. Don't call her for the room number from the lobby or standing just outside of the hotel. Walk with a purpose through the lobby, to the elevator and up to her room. When she opens the door just walk right in, don't stand in the hallway and tell her how beautiful she looks. Many girls will not stand in the doorway at all when answering but rather behind the door.  Just walk right in as if you belonged there.

I usually give gentlemen a general enough description of how to find my room so that they can walk in looking like they belong there. When you call your lady friend and she gives you her room number, ask her which direction you should go to get to the elevators

appointment is during the day.  A lot of hotels have meeting space on the 2nd or 3rd floor so you will fit right in as you take the elevator to the 69th floor where her room is located.

Walk right in like you belong there.   Chances are that the desk clerk has no clue whether or not you are a guest or not.  If you act like you know where you going, you will not have a problem.

Just don't hang around the lobby, looking confused.  Just go straight to the elevators and you will be fine.

Swim

This is simple...........

Try to find the hotel website and check the description, pictures, outside etc. Also check out the hotel info on various booking related travel websites.

Call the front desk pretending you have a reservation or want to book a room and ask a few questions like rates, pool, meeting rooms etc.

If you leave in the area and the hotel has a bar visit a few days before for a drink and do a dry run, scope the outside before the date.

Depending on the time, enter with several people together or follow guests straight to the elevator.

Again depending on the time, if the hotel has a seminar, convention, pretend you are a part of it and work your way from outside the seminar or convention room.

Now if for whatever reason you get questioned, pretend you are at the wrong hotel with a comment like "This does not look like the hotel I checked in at," front desk will be willing to give you directions outta there - just be ready with the name of a surrounding hotel.

Also if questioned, you can always pretend you were looking for the bathroom. Almost all hotels have at least a semi-public employee bathroom. In most cases staff / security will be only happy to give you directions to the bathroom and leave you alone.

If this is a nice big hotel, always have some spare dolla bills on you. Be nice and take good care of the porters and they will bail you out most of the time. Their mission is to take care of the guest and make some $$$. Nothing more or less!

I wear jogging shorts and a Tshirt and splash some water on myself right before I go in the lobby..and carry a water bottle..If I don't know my way around I tell security I just ran twenty miles and ask them to guide me to the elevator as I am disoriented

Re: a strange hotel

Or...you could stage a distraction.  Perhaps pull the fire alarm or have a friend drive their car through the lobby?  You are thus free to quickly move unnoticed through the entrance.  You should probably crawl on all fours to avoid the robots spotting you...

Re: no worries.

I was like you the first time I was meeting my provider, but as soon as realized, who the heck lives in a hotel? They get strangers everyday.

so..don't worry about it

This is so much easier than you would think. I spend more nights in hotels than I do at home. As long as you are not acting really weird, dangerous or confused, nobody will likely say anything to you. If they ask if you need help, you can always smile and say "No thanks" . You don't have to to tell them anything and they won't press you unless you are acting weird. If you feel compelled to say something ask where the gift shop is. Just don't blather on about forgetting your toothbrush or buying a souvenir for your grandmother.

And by the way, next time you are in a big hotel lobby. look around and see how many people are talking on their cell phones - probably half. So you can do that too. If you are nervous and concerned that someone will start talking to you, mindlessly prattling away on your phone will be good cover. It will make you look like half the other people in the lobby, will prevent people from talking to you, and will provide some logic as to why you are wandering around a bit - you're distracted by your phone call! Nobody will know that a lady just gave you a room number and hung up. Just keep talking as you walk to the elevator - talk about sports, or some project at work, or what your friend did last weekend. Just don't have a short, furtive conversation and then nervously scramble around looking for the elevator.

About the worst thing that could happen is that you act so nervous or weird someone asks if you are a guest at the hotel. Don't say yes, because they will ask to see the room key. If you say your wife/girlfriend has it and is going to let you in, you're screwed because they'll ask for the name and room number and of course you won't have the name she registered under. Best bet is to say that a friend is meeting you in the bar, and by the way, where is the bar, and is that the only bar in the hotel. At that point, about all you can do is call the lady, tell her you got challenged and see if she will come get you in the bar.

In 30 years of traveling, staying in all types of hotels all over the world, I've never had anyone challenge me in any hotel whether I was a guest or not.

Another thing, try to either board an elevator alone, or if others are aboard, be the last one to push a floor button - that lets you see where others are going; if someone else is going to the floor that is your destination, just push a higher floor, then get off there and catch one back down after a few minutes - that way you avoid the awkwardness of standing in the hall and knocking on a door while the other folks use their key to enter the room next door.

My last experience... (it's a funny story i think)

I was to go to a local mid-level hotel that holds a lot of conferences, but alas none on this day. Now I'd been there before, in fact just 2 or 3 weeks prior to see someone else so I knew the layout.

She got upgraded so only elevator #1 went to her floor w/o a room key. Problem was elevator's 2 and 3 were the two always in service.  I stood around the lobby hitting buttons, getting frustrated as my time ticked away.  Finally, I just jumped in and went to another floor so as to not stand in the lobby like a clueless tourist.

I got to X floor and kept playing w/ the other elevators sending them down to other floors when I wanted to go up. Cleaning lady walks by see's my jabbing the stupid buttons and just looks at me as I walk in the elevator, hit a button, walk out, stand there all pissed off and then hit the up button.  I must've spent almost 10 min throughout this ordeal.

Finally, someone on the floor I was on comes out of her room and presses the button and BAM!!  Elevator #1.  (WTF I'm thinking..., but hey I finally got it).  We go down to the lobby and as the door opens I stay inside to see the same lobby people just staring at me in the elevator as I press the button and wait for the doors to close.  In jest I pass off some half-assed wave and a smirk and finally go up to my destination.