Woooo I have a date! (I Think)

Miscellaneous and Personal Stuff I Must Share
1

Background: I am 28, my dating experience so far is this:

In high school I chased after one of my best friends who I never had a chance with. Right before I left for college I was asked out by a girl from work. Before we went on our first date she would call me at 10:00 pm and talk for hours (she would talk I never said much.) On our first date we did several things, went to the dam, a movie, ice cream and then we picked up my gay best friend. During the trip to my friends house my date tried to talk my gay friend into dating her when I went to college. Later that night, she said that she loved me. I told her I didn’t feel that way but later when she asked me to kiss her I did. Since the whole day freaked me out I broke it off the next day.

In college I was set up on a blind date by my mom when I went to home. The first night was fun, saw a really crappy movie, we laughed at it. We stopped by her work so she could pick up her schedule for the next week. Her ex-boyfriend saw us and apparently he saw us. Later that night he called her and threatened her. we went out the next night and had a picnic in the woods so no one (her ex) could find us, the date went well. I had to go back to college the next day. We played phone tag for a little bit and then lost touch. I hope she is OK.
Later in college me and one of roommates went to a one a his friends house (a girl.) We all got drunk and thing got a bit crazy. We all ended up naked and inches away from a full on threesome before she said no and we stopped. Later that night she offered to have sex with me but I got it out of her she only really wanted to because she a had a crush on my friend and he asked her too (he was a jerk but one of the lovable jerks.) I told her she was beautiful but no if we had sex it should be for the right reason. She went to sleep in her bed, I slept on the floor somewhere.

That is my dating experience. Most of college I was never really looking and the girls that I had any interest in always placed me into the dreaded “Nice Guy” group. Later I fell into a pretty severe depression and didn’t look or care to look. Now I a getting my life back together and not as depressed so let look at my current scenario. Oh yeah if you haven’t noticed my now I have a tendency to over-think things and I know crap about “Playing the game.”
The Current Scenario:

I was recently in a show at the local theater. There I met “Kay”. Kay was the stage manager, when I first met her I thought, “Oooo Cute.” Then I noticed she had a teenage son. I thought, “Damn Married,” and took her off the “Possibility List.” As time goes on I notice there is not a ring on her finger. As we get close to opening night she and a another cast member she is friends with, “Tee”, asks for a cigarette, they doesn’t normally smoke but theater does that to some people. I give them each one. For the run of the show they both are bumming off me and I freely offer most of the time. I know that Tee has a boyfriend but I never hear anything about a significant other from Kay. What I do learn in the coming weeks is that Kay is 35, her son it 13, she is smart, funny and pretty, I can make her laugh, she is the manager of a department that works with disabled children and I like her.

The last weekend of the show Kay says that she wants to but my a pack of cigarettes for all the ones that she has bummed. I get up the courage to ask her out. This is approximately how the conversation goes down.

Kay: I will have a pack of smokes for you tomorrow.
Me: You don’t have to do that. To pay me back let me take you out to dinner.
K: Ok.
Second
Second
Second
K: Wait a second how does you buying me dinner pay you back for the smokes.
M: Well, I get to spend time with you.
K: Ok but I have to buy you dinner.
M: Thinking about it.
M: Ok that wo’t kill my sense of manliness too much.

Then a meeting is planned for dinner this Friday.

Since last Friday and today Wednesday this a synopsis of what has happened:

She has made a couple a references about me being younger than her.

The cast went out to dinner on Saturday, I ordered cheesy fries Kay and her son ate half, then they ordered cheesy fries and I ate half of theirs. We all had a fun time and I spent most of the time talking to Kay and her son. When we were leaving she is in front of me in line and sneakily pays for my dinner. I tell her she didn’t have to do that and we still have dinner on Friday. She says she knows and that she is still paying for that she makes a lot of money. I agree but we need to see a movie and I will get that. She agrees.

I am telling the people that I like at work I have a date on Friday and now that I type this it seems that this might really be a date. That is not saying that if we are just going out as friends I won’t have a great time, I get to spend and evening with a smart, funny and pretty woman. I really want this to work into a romantic situation though. I am 28 and have never encountered any real romance in my life and I feel like am missing out on one of life essential experiences.

So I ask you great and wise members of the SDMB do I have date or am I meeting up with a friend and if I do have a date do you have any advice.
P.S. It took me almost two hours and two liters of beer to type this so I am going to post it but I just found a flaw in my post. Kay who is a smart and funny person is a perfect candidate to be a member of the SDMB. Kay if you do read this and you know who you are and who I am, then I hope you see this as a portal in to my lonely but loving soul.

etgaw1

2

Dude, don’t you REALLY need to pee? Go ahead, I’ll wait…

Oh. My advice? RELAX!! What’s the worst that could happen? It’s obvious she likes you, and even if nothing else develops:

That’s good isn’t it? Anything beyond that is gravy.

3

The beer really shows.

I will second WTS? opinion. Just go there and enjoy it. You don’t need to put a label on it. I can’t tell you how many relationships I ruined trying to put labels on them.

4

You are right. At the very least I get to spend an evening with an amazing person.

Mostly I needed to get my insecurities out and ask for advice in wooing this beautiful woman.

Oh and I did pee once while I was writing the OP and a couple of times since. And once while writing this message, I feel better.
etgaw1

5

I think you’re in great shape.

Just don’t take this one to the dam. :slight_smile:

6

Congrats! Just be yourself, don’t second guess the moment, and have fun. :slight_smile:

7

I think it’s a date, and I think Kay likes you, too. Here’s a little perspective from Kay’s side - she’s 35, and she is a single mom of a 13 year old. A (I’ll assume good-looking) 28 year old showing interest in her is making her day. She’s probably used to guys finding about her kid and making a guy-shaped hole in the wall. At 35 with a dependent, she’s probably mature enough to figure out that the nice guys are where it’s at, baby. Go out, have fun, and don’t overthink it.

“Lonely but loving soul” - that could have described my husband when we met seven years ago (and me, too, frankly).

8

Lol! This thread’s got what, 6 replies, and already someone’s said what I came to say! That’s the Dope for ya…

Anyway, I came to say exactly what featherlou already said, which is don’t overthink it. A lot of people who don’t have a lot of experience romantically treat any experience like the chance of a lifetime, and try to make every single thing they say or do matter, and thus come off as overeager. Really, just be yourself. Let her think you have no expectations, that you’re just there to have fun regardless of the outcome, and let things progress naturally.

Above all… don’t ask her if it’s a date. Don’t even say the word “date”. It just dumps unnecessary pressure and tension onto the situation.

And most importantly, have fun! :slight_smile:

9

Go to dinner, have fun, enjoy yourself, worry (or don’t) later. Just take all the pressure off.

Also, I want it on the record that I fully support dating your stage manager, just don’t make her life hard by giving her trouble at work. If she never has to ask you to be quiet backstage or ream you out for being late, there won’t be any kind of conflict-of-interest, and that will keep things simple.

EDIT: I see the show’s over, so the last bit of advice may not apply.

10

Dude, it’s a date! Have a nice dinner, have some nice conversation, and have some nice sex! You deserve it!

11

this is totally out of the blue, but based on what you have said… rent “Harold and Maude”…

its a movie about a lot of things… but the first of them is about losing your insecurities (about being who you are)… ((sure it has a plot with an young guy with an older woman, but in this case I don’t relly think that applies))
I’m just saying…

fml

12

Thanks for the advice everyone. I will do my best not to over think things but that is easier said than done. Hopefully I will just get it all out before Friday.

As for the date details. 6:00 we meet at her house. Then we go to dinner, her choice. 8:00 we are going to watch “Ocean’s 13” Unfortunately no matter what the date will be over after that because I have to go to work at 5 the next morning.

I do feel better now. I will update you all when it is over. Please keep your advice coming even the obviously bad advice so I can start to laugh at this it will help me from not over thinking.
Thanks all

etgaw1

13

This is a good thing, it’s better to keep it short and simple to start out with. And a bail out excuse if things get awkward and you’d like to catch your “wooing balance” for the next date.

14

I suggest the popcorn trick.

15

What bad advice? This stuff is all gold, baby.
:wink:

16

Well everything up until the popcorn trick was gold I agree, now I am asking for bad dating ideas to make everyone laugh since this is a thread on dating. Or you can post first date horror stories so I know what not do. Remember I am a bit of a novice at this.

As for cutting a hole in the bottom of the popcorn and sticking my junk in it. No thank you. Going to the hospital with second degree burns on etgaw2 is not my idea of a fun time and then I would have to go to work the next morning and stand in front of a griddle with a sore peep not gonna happen. Next Idea. Of course it would make for a interesting story if things did take off.

17

THAT’S the popcorn trick?

18

I met my husband when he wa 30 and I was 38 and we’ll be married 5 years in August. I made several references to our age difference so he wouldn’t lose sight that I was 8 years older than he was. Turns out, he’d figured it out.
He’s so bright!

19

To once again quote my friend Rob, “dont forget to slip her the sausage.” :smiley:

20

One first date horror story coming right up. Not all that bad, but a bit embarrassing at the time.

It was my very first date ever. I had finally talked my parents into letting me borrow the car to take a girl to the movies. I grew up in a very small town, so going to the movies meant a 20-odd mile drive to the next town over. I pick girl up, drive to the fancy new cineplex and park. We sit in the car for about five minutes discussing which movie we’d like to see. We get out, lock the doors and head into the theater. About the time that I slammed my door, I noticed the keys still in the ignition. Girl also noticed it at the same time I did, so there was no way to avoid the embarrassment of the situation. :smack:

Resolution: I called my dad from a pay phone (remember those?) inside the lobby. He drove down, unlocked the car door and placed my keys under the driver side seat. It ended up being the only date that this girl and I ever went on. My dad waited almost a week before laughing at me about it. It did teach me an important lesson about checking for my keys before locking the car.

-Belz