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The First Date Game Plan.

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Please excuse the corny thread title, lol.

I'm looking for some opinions & suggestions for the plan I've created for my first date, my goal is to make the day/night memorable for the both of us.

I'll first take her to Milestones at Dundas 24 for a light lunch at noon time, then perhaps a movie or some shopping time.

I, then will take her to a Cirque Du Soleil show (surprise) and expecting the show to finish at around 6pm. At this point I'd like to bring her somewhere, a place where we can have a cocktail or maybe a glass of wine before dinner, if somebody could recommend me a good lounge to visit preferably close to Splendido, that'd be great! (Currently considering C5 Lounge OR One Restaurant.)

Then, I will be taking her to Splendido for dinner and desserts and planning to end the night at Panorama.

I'm pretty much set on Milestones because the AMC theatre is right beside it, I was thinking C5 Restaurant and Lounge might be a cool place to take her to for a drink before dinner, and as for Splendido, I'm expecting excellent food, wine, service, with touches of romantic atmosphere and at Panorama, I'm expecting a nice view, a little privacy and romance to end the night.

On a side note, I will not be driving after the Cirque Du Soleil show as I will be drinking before, during, after dinner. My car will be parked at Yonge/Carlton area, so from that point on I'll be taking the cab or walking to our first lounge.

I don't mean to sound ignorant but money is not an issue. I'm open to all suggestions/alternatives to restaurant and lounge choices, even any interesting things that I should check out, I'm open to it. Would really want to nail this and have a smooth sailing first date. Would prefer to keep the area within downtown.

Thanks everybody!

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  1. Since you asked for opinions, my first thought is: Whoa!!! That is entirely too much date for the first date. I think you've packed at least three dates into one marathon outing. I couldn't even stand that much time with Mr. Rabbit (just kidding, Mr. Rab!). It feels like you're trying too hard.

    As for the specifics of the plan:
    1. You're probably not going to get a lot of people around here to actively endorse Milestones. It's a safe chain pick, but I get why you want to go there given proximity to the theatre.

    2. I wouldn't do pre-dinner cocktails at C5 because the interior bar space is kind of disappointing. The dining room is very pretty with interesting views, but the bar itself is sort of dark and bla (in my opinion). The bar at One would be much more exciting. It's a scene-y place for drinks and probably a good pick (if that's what you're looking for). The other spot in that neighbourhood I might consider is Avenue at the Four Seasons. More staid than One, but a classic.

    3. I haven't been to the new Splendido, but I don't think you can go wrong there!

    4. I prefer the Park Hyatt to Panorama. Both have a city view and romance factor (actually, I don't think Panorama is romantic... I've always found the decor kind of weird), but the Hyatt is more grown up (IMHO). Although if you take her to the Seasons for pre-dinner you probably don't want to do more than one hotel bar.

    Good luck with your date. She must be a special girl for you to undertake this much planning!

    1. Rabbit is correct, I also thought you've packed four dates into one. What if she gets tired of you after lunch? What are you going to talk about by the third micro-date? And Milestones? I've never been, but I'll be dragged there kicking and screaming this Friday when a bunch of engineers from my wife's company go out for their yearly dinner. I don't think that Milestones and Splendido go together. With so much going on in one day, you've got more chances to not have a smooth sailing date. (just my honest opinion)

      1. Skip Milestones and get schwarmas at Milo's pita instead.

        1 Reply
        1. re: haggisdragon

          you're nuts

          I'm going to sound rash:

          The food doesn't have anything to do with the outcome of the date. It is personalties involved that will determine the outcome.

          But what the hell do I know, this is a food site.

          As I have previously mentioned in another post. Its always good to have an emergency means of egress. Finish the date at Utopia cafe, and by that time if you don't like her, eat the double burger so she will be so distributed that she won't be interested anymore (unless she is also burgerphile in which this won't work). And don't you for one minute think she doesn't have a backup plan of her own!

        2. The original comment has been removed
          1. I agree with the others, this is too much for a first date---unless this is someone you are already good friends with, know well, and have decided to push it into the romantic realm (and are certain she has the stamina for an all-day extravaganza). Since you already have the Cirque d' Soleil tickets, why not go to a wine bar for a glass or two and some small plates. Then--surprise!--take her to the show. If she's still having a good time, take her out for dinner afterwards. Most likely you'll both be hungry again by then.

            Don't overwhelm the lady. You don't need to sell yourself so hard, either, by whisking her from one place to the next. Remember, the point of the date is to get to know each other better and see if the chemistry is there. Good luck!

            p.s. are you sure she won't have made evening plans with her gfs to debrief on your "afternoon" date?

            13 Replies
            1. re: ChristinaMason

              Don't be discouraged, we want your date to go well, but I do think your day of activities is going to be too much. Although I haven't dated in over ten years, I think if I was faced with that type of a day I would be overwhelmed and quite possibly turned off... you may come across as desperate.

              I think ChristinaMason has the right idea, a quick bite to eat and a show afterwards is the way to go. If you're both still enjoying each others company go for dinner. Don't set too many expectations or you may be very disappointed in the end.

              1. re: ChristinaMason

                I'm with Christina, Rabbit, and everyone else here - a first date that somehow turns into a 12-hour date is wonderful. A first date that REQUIRES 12 hours (and that much expense) is just too much for any woman I know. If she's expecting a lunch-and-maybe-a-movie afternoon date, you are seriously overbooking. I think the wine bar/small plates thing is a great idea - sharing food gives you something to talk about, and there's an intimacy there that you won't get sitting in a movie theater. Caren's might be nice, without being overwhelming.

                Then again, you know this girl, and none of us do. If you think she's the sort that requires this lavish of a first date, then I shudder to think how you're ever going to come up with a second. Pace yourself, man - I'm sure she's worth a million bucks, but that doesn't mean you have to spend it all at once. :)

                1. re: Wahooty

                  Also, what will you do for the next date?
                  She will be busy on the Stairmaster!

                  1. re: Wahooty

                    I just got a brainwave, he should bring her to the Chowmeet coming up soon.

                    We are hitting two places, Southern Rub BBQ and Chicago Pizza Kitchen.

                    1. re: foodyDudey

                      I also think a meet full of 20 rabid chowhounds would be a wee bit on the overwhelming side. ;)

                      1. re: foodyDudey

                        Thanks to all the replies, oh boy am I glad to have posted this here. To reply some, yes she is one very special girl and to reply the others, she said she will be spending her whole day till night with me and asked me to be in charge of planning. I'm not really trying hard to impress her (okay I lied) but I honestly ran out of ideas of what to do in between times like, after the Cirque Du Soleil show and dinner at Splendido.

                        She also mentioned that she's not familiar with downtown and we both enjoy drinks so I figured, hmm, maybe we should check out lounges together.

                        I can only say, the main events are Cirque Du Soleil and Splendido, these 2 are musts and I was only thinking the other places I've stuffed into the plan would compliment the main events and also give us something to do or somewhere to be at.

                        and I do apologize if I might have confused some of you (in fact, I think all). This is our first OFFICAL date, but we've known each other for awhile and have had casual lunches/dinners but nothing really special. Maybe it doesn't even qualify as the "First Date"... and it was never my intention to turn this thread into a "dating topic" as I feel that's probably what some viewers may think.

                        Anyway, I'll review the plan and take out some ideas, but after all, she is expecting to spend the whole day with me.

                        About the smooth sailing comment, I can only agree with you as it is true, this could probably be the true beauty of less is more and about the Utopia comment, it made my day!

                        Thanks all!

                        1. re: ekk20

                          How about going to the Museum after the cirque? (depending on when the show is) You can kill some time and go to C5 for a drink, then Splendido is not far away - you could probably walk over.

                          1. re: ekk20

                            Also, the Gardiner Museum is across the street from the ROM, if you like ceramics. A walk around the Distillery district in the afternoon is rather nice too. Can do coffee. Restaurants are only so-so, but there are galleries and artsy shops to stroll around in.

                            Good luck!

                            1. re: jlunar

                              I second the Distillery District for either before or after Cirque. Do some beer tasting at Mill St. and have a Mayan hot chocolate shot at Soma (and stock up on the best chocolates in the city).

                            2. re: ekk20

                              Thanks for cluing us in...and good luck! Sounds like you won't need it tho. What a thoughtful guy :)

                              1. re: ChristinaMason

                                Many apologies once again about the lack of proper information in my original post.

                                I just called Splendido and made reservation for 8:30pm, the other only available time was 6pm which I couldn't make because the Cirque show ends at 6pm earliest, starting at 4pm.

                                I now find the distillery district rather interesting as we both have never been to, so spending an afternoon there would be interesting, I imagine. I need to think harder for something fun to do in between Cirque and dinner. Was originally considering checking out one's or C5 but I do think it might be best to leave that until Panorama.

                                Thanks for all the generous replies.

                                Cheers.

                                1. re: ekk20

                                  Definitely the Distillery district for a diversion. The Mayan hot chocolate is a fantastic recommendation, great stuff and a great venue. You might also want to try some of the galleries in the area, and I think that there is a place that will let you do a glass blowing class, or you could do a segway tour.

                                  1. re: ekk20

                                    Just have a drink w/i walking distance from Splendido. There are plenty of restaurants that can facilitate that. 93 Harbord, Harbord Room, Loire, etc....these are all a few mins away.

                                    C5 is a 15-20 min walk from Splendido at least.

                                    I still think you're blowing your load for a first date. Don't over-plan, girls like spontaneity.