First Meet/Date turned out to be a Disaster and I will learn from this in the future

[Alpacalia]

My father brought my mother along to shop for underwear for his older brother for their first date. 

I think a good rule of thumb is to plan a date so that you have a good time and to show your level of interest but not spend too much time trying too hard in case things don't work out.

[Stupidkupid]

2 hours ago, d0nnivain said:

They had a pre-arranged plan to go to the waterfront area.  The OP simply hadn't selected a restaurant in advance, which became a problem w/o a reservation.  

Sorry, that's what I meant. Waterfront wouldn't be enough for me. I want to know exactly where I am going as it gives me an idea of what to expect, dress for and prepare for and also, how easy it is to get away if its awful

[SumGuy]

22 hours ago, IntBrowser said:

... So I just gave up and told her to drop me off at the supermarket and went home.       I felt like she wasnt putting any effort into coming up with something to do and it was all me coming up with places to go.    .... 

She was the chauffer, she was contributing big time and not sure what you expect of her, to pull some magical place out of a hat.   Also don't you both have smart phones?  Just search for a place near you, look at the map, perhaps call ahead, get take out, find someplace warm to hang out that is not the car even if no food....etc., etc.   Seriously all you need is a wamr place to talk, you can get food and drink anywhere and take it there.

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I didnt want to say "wannna just come back to my place" since I couldnt think of anything else to do.     

Why not?  It's not like you planned this or it would seem like you did.  You can acknowledge you wouldn't normally do this, not offended if she wants to text someone to let them know (safety you know) etc.   If there really was no place to go or no place to park I'd suggest this right off...go by a store and get stuff.  Now if you place is a disaster, yah maybe you are a bit nervous.

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keep asking myself what would I have done differently if put back in that situation and I can't think of anything I would do differently because the parking factor killed the meeting.   

  That is a very can't do attitude.   There has to be more than one place to park or to go to.  See suggestions above.   Being able to think on your feet and address a problem with good humor is an attractive quality.  Also, yes next time plan ahead better.

[d0nnivain]

37 minutes ago, Stupidkupid said:

Sorry, that's what I meant. Waterfront wouldn't be enough for me. I want to know exactly where I am going as it gives me an idea of what to expect, dress for and prepare for and also, how easy it is to get away if its awful

I get what you are saying but I also assume that "the waterfront" is a defined area.  In my town people go to the plaza.  There are 4 dining restaurants, 3 bars, a smattering of deli's, ice cream parlors, coffee shops & other businesses in the area about the size of a town square.  It's possible to go there & walk around without a specific restaurant  or other entertainment venue selected in advance.  They all have similar dress codes unless you are specifically going to a wedding at the one place.   Knowing that general destination even if not the exact restaurant would be enough for me because I would still have the info you desire in advance:  what to expect, how to dress & how to get away.   In the old days before Covid, I would probably be happier with sort of a walk through the plaza / water front & discussing the dining location to make a joint decision based on what looked good in the moment.  

[Stupidkupid]

Just now, d0nnivain said:

I get what you are saying but I also assume that "the waterfront" is a defined area.  In my town people go to the plaza.  There are 4 dining restaurants, 3 bars, a smattering of deli's, ice cream parlors, coffee shops & other businesses in the area about the size of a town square.  It's possible to go there & walk around without a specific restaurant  or other entertainment venue selected in advance.  They all have similar dress codes unless you are specifically going to a wedding at the one place.   Knowing that general destination even if not the exact restaurant would be enough for me because I would still have the info you desire in advance:  what to expect, how to dress & how to get away.   In the old days before Covid, I would probably be happier with sort of a walk through the plaza / water front & discussing the dining location to make a joint decision based on what looked good in the moment.  

And, of course, she could have asked the actual plan.

[IntBrowser]

8 hours ago, SumGuy said:

She was the chauffer, she was contributing big time and not sure what you expect of her, to pull some magical place out of a hat.   Also don't you both have smart phones?  Just search for a place near you, look at the map, perhaps call ahead, get take out, find someplace warm to hang out that is not the car even if no food....etc., etc.   Seriously all you need is a wamr place to talk, you can get food and drink anywhere and take it there.

Why not?  It's not like you planned this or it would seem like you did.  You can acknowledge you wouldn't normally do this, not offended if she wants to text someone to let them know (safety you know) etc.   If there really was no place to go or no place to park I'd suggest this right off...go by a store and get stuff.  Now if you place is a disaster, yah maybe you are a bit nervous.

  That is a very can't do attitude.   There has to be more than one place to park or to go to.  See suggestions above.   Being able to think on your feet and address a problem with good humor is an attractive quality.  Also, yes next time plan ahead better.

its been times in the past I planned a date and we both found out it was closed down lol    I used to say........Only me and had no back up plan

[IntBrowser]

8 hours ago, d0nnivain said:

I get what you are saying but I also assume that "the waterfront" is a defined area.  In my town people go to the plaza.  There are 4 dining restaurants, 3 bars, a smattering of deli's, ice cream parlors, coffee shops & other businesses in the area about the size of a town square.  It's possible to go there & walk around without a specific restaurant  or other entertainment venue selected in advance.  They all have similar dress codes unless you are specifically going to a wedding at the one place.   Knowing that general destination even if not the exact restaurant would be enough for me because I would still have the info you desire in advance:  what to expect, how to dress & how to get away.   In the old days before Covid, I would probably be happier with sort of a walk through the plaza / water front & discussing the dining location to make a joint decision based on what looked good in the moment.  

waterfront is a long walk area facing the river with seating areas under the trees