Ask a friend to dinner during our vacation?

My friends Cindy and Bill are on a weekend trip to Chicago with me right now. Bill goes back on the train Sunday afternoon, but Cindy and I stay till Monday night. We actually crashed in the same bed last night while Bill took the second. Lol.

So, lately we've spent more time together, especially one-on-one, and I've been trying to think about how to ask her out. Since we're already friends, it feels trickier, but I thought once Bill leaves Sunday, maybe I could invite her to dinner or something? Any ideas are helpful.


What Girls Said 1

  • Try to ask her to hang out just the two of you. Through the date be more playful/flirty towards her.

    • You mean, once we get back? I mean, it will just be the two of us anyway this evening and tomorrow.

What Guys Said 1

  • It would be easy to ask Cindy what to do with the remaining free time when in such a city offering a myriad of opportunities. If she has a good time, then everyone will have a good time... correct?

    You didn't say if C&B were an "item" ... seems important to your Q

    • We're not. Want us to be, hence the Q. Lol

    • Show All
    • Well, we had existing plans for today, but not only did she feel tired by midday yesterday, she developed a migraine and was happy to return to the hotel and nap by 6. I also noticed evidence of it being a time of the month for her, which could have added to her feeling lousy. Point is, not good way/time to suggest fun evening plans.

    • You shower first, arrange Champagne in hot tub to soak, epsom salts if available for her privacy, then she comes out in soft robe to room service fancy dinner, either by the window or TV movie.