So my situation is a bit tricky, in my opinion, but I thought it might help to get advice. So...

I'm 23. I have a "first date" coming up with a guy I've liked for a while. He actually went to my high school, but I didn't know him at the time, only who he was. He's about 25. At some point, he and I started talking while I worked at a Starbucks. This past summer we talked a bit on the phone, but didn't see each other because he was elsewhere for the summer. Now that he's around and I'm actually single, he called to ask me on a date with him.

I'm actually really excited because the date sounds excellent. We're going downtown, maybe doing a little Christmas shopping, then having dinner and going to see a play. Dinner and play will also be with his brother and his wife. Afterward, I'm assuming we'll probably go out.

The problem is... he is planning on getting a hotel room because he doesn't want to drive home late at night, and he said his brother and his wife will probably do the same. He didn't seem to be expecting that I would stay with him, but just wanted to let me know so I can make plans. I would like to stay downtown too, but I can't afford my own hotel room in the city. What should I do? I'm not completely opposed to sharing a room, but I don't want it to be assumed that "one thing will lead to another." This is a first date!

Any advice you can offer me? About what I should do, or what I should say, or even what he may be expecting?

Thanks!
Sarah

Maybe ask him to get a room with 2 beds in it if you aren't comfortable sharing a bed with him.

When you say you're going down town, do you mean as in 90 miles away or 10 miles away from your home? If you're talking 10 miles away then you should bring your own transportation if he's not willing to bring you back home. If you are talking more like 90 then you need to get your own room and if he's a real gentleman he will at least pay for half of it. I'm sorry but it sounds like he's got a plan to get lucky.

No, I would not share a room with him. First date? Keep it as you have described and it sounds like a lovely date. But sharing a room with him is going too far. Even if he gets room with two beds - excuse me, but since when has two beds stopped any activity?

If you cannot take your own transportation and he cannot take you home, then reconsider either the date night or simply getting your own room for the evening.

It is according to your own virtue, but being the traditional guy that I am, I would never propose that on a first date. I have had women come in and mention staying the night on a first date, or propose me staying at their place. I didn't, and never heard from them again, which is fine with me. You could always get a taxi and ask him to pay for it, if he can't do that, then you don't need him anyway.

Sounds a bit pushy and sounds like he was hoping to get lucky on that first date, esp since he knew you already from before.

I would come back and not accept date unless it will be under the terms that is good for you, if he is not bringing you home, and you don't have your own transpertation, cancel and reset for a new date when he can treat you properly

One of the few tricks in the book: Yeah, I'm too tired to go home so I'm getting a hotel room... oh, by the way, my _______ (insert relative or close friend) and his ____ (insert girlfriend/fiance/wife) are doing the same too. Let me know what you want.

Stand firm in what you believe in. You don't feel comfortable spending the night with him, tell him you're going home. Even if you do get your own room, chances are, he'll ask to "hang out because he can't fall asleep"