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Old 06-10-2015, 05:34 AM
 
213 posts, read 508,886 times
Reputation: 113

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Long story short:

I've haven't been in a relationship for several years and have been variably single/floating along w/one night stands. Lately I've been vibing well w/this girl who I work with (I know, I know...I've thought long and hard about the consequences, but there's enough distance between us at the workplace that it could possibly work), and finally had the gall to ask her on a legit one.

We've already hung out for lunch several times, which allowed us to build up a friendship and know each other relatively well. I've initially settled for dinner+movie, an option that many have discouraged as it's cliche and leaves little time for chit-chat.

Apart from feeling out of my element after years of un-dating, I'm puzzled as to how to put together an entertaining date for a girl I've known for a while. Ideally I would've asked her out much earlier, but spent much time mulling over the possible drama/gossip at the workplace before I pulled myself out of my head.

Any advice/constructive criticism you guys could offer me? Any help would be appreciated, thanks.
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Old 06-10-2015, 05:57 AM
 
Location: Southern Illinois
10,363 posts, read 20,805,729 times
Reputation: 15643
My best advice is don't overplan--like a walk in the park is fine and gives you a chance to talk w/o the pressure of staring into each other's eyeballs. With what you have already planned it would be a good extra. And then just go with the flow.
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Old 06-10-2015, 06:30 AM
 
745 posts, read 802,055 times
Reputation: 695
Jerk off earlier in the day. It will clear out the gum and you won't be a "2 pump chump" if you end up getting lucky...
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Old 06-10-2015, 06:31 AM
 
3,850 posts, read 4,155,400 times
Reputation: 7868
During your friendly lunches, what have you learned about her interests? When I was dating, my idea of a great first date was a sporting event. If you know what she enjoys doing, you could plan an active date that's casual and fun. Good luck!
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Old 06-10-2015, 06:39 AM
 
Location: NY
9,130 posts, read 20,021,316 times
Reputation: 11707
The two of you do not need to "get to know" each other like two strangers going on a date. You have been doing that already. So no need to sit across from each other for two hours to "talk" over dinner, drinks, coffee, etc.

Do something fun and interactive together. Something conducive to talking, but also conducive to enjoying something jointly. Then just be relaxed and enjoy the companionship. No need to go overboard. Let things develop naturally.
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Old 06-10-2015, 07:36 AM
 
2,669 posts, read 2,093,849 times
Reputation: 3690
I would discourage you from going to the movie. You will have no chance to talk and look at each other and it is too early for you to cuddle and make out

A walk in the park, maybe to a local fair or outside event or to a museum sounds a lot better. Followed by drinks and appetizers somewhere. That would be my recommendation.
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Old 06-10-2015, 10:28 AM
 
Location: Portland, OR
9,855 posts, read 11,937,175 times
Reputation: 10028
I'm hanged as to why two people who have hung out for lunch several times and gotten to know each other relatively well need to dinner and movie at all. Unless they both want to see that particular movie and eat at that particular restaurant. But that doesn't sound like whats happening here. It's like ooohh I like this girl I'm going to rewind back to go and start dating like we never met before. Sigh.
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Old 06-10-2015, 01:36 PM
 
33,387 posts, read 34,858,743 times
Reputation: 20030
Quote:
Originally Posted by Raymond Stereo View Post
Long story short:

I've haven't been in a relationship for several years and have been variably single/floating along w/one night stands. Lately I've been vibing well w/this girl who I work with (I know, I know...I've thought long and hard about the consequences, but there's enough distance between us at the workplace that it could possibly work), and finally had the gall to ask her on a legit one.

We've already hung out for lunch several times, which allowed us to build up a friendship and know each other relatively well. I've initially settled for dinner+movie, an option that many have discouraged as it's cliche and leaves little time for chit-chat.

Apart from feeling out of my element after years of un-dating, I'm puzzled as to how to put together an entertaining date for a girl I've known for a while. Ideally I would've asked her out much earlier, but spent much time mulling over the possible drama/gossip at the workplace before I pulled myself out of my head.

Any advice/constructive criticism you guys could offer me? Any help would be appreciated, thanks.
my advice is;

1: do not rush things, take them as they come

2: regardless of what you do on a date, always make your girl feel like you really want to be with her, and not just get into her pants and move on to the next girl

3: take what she is willing to give you. if at the end of the date she lets you kiss her at her door, and then goes in alone, accept it because she isnt ready for more. if she invites you in, and decides on a roll in the hay, take your time with her, and revel in being with her.

in the end you always want her to know that you are where you want to be when you are with her, and that she is the only person in your world. if you try to push for more than she is willing to give, then you risk getting what you want, one time and never again, as well as losing a friend.
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Old 06-10-2015, 02:51 PM
 
Location: Viña del Mar, Chile
16,391 posts, read 30,942,753 times
Reputation: 16643
Best advice is don't think about it, don't worry and just go.
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Old 06-15-2015, 08:00 PM
 
213 posts, read 508,886 times
Reputation: 113
Update:

We had dinner on Friday night and then took a long walk. We talked, we laughed, we vibed, we flirted...we had fun. She'd suddenly gone cold towards the end of the date which both baffled and worried me. I touched base w/her on Sunday to ask if we were on even keel...said she thought about things and concluded that she doesn't have romantic feelings for me. She mentioned there being an initial spark when we first started hanging out and expected her feelings to grow beyond friendship after the date...but they didn't for reasons unbeknowst to her.

I did the right thing and thanked her for her honesty, adding that I'll dial it back for both of our sakes. Still, this one hurts, a lot. I've bared my soul, as has she (to a lesser extent) over the last couple of months, and I genuinely felt like there was a strong connection between us before things went south during the end of that date. I've been wracking my head by rewinding the date; did I come on too strong? Should I have held her hand? Should I have been more confident?

She wants to maintain some level of friendship as she enjoys my company, but I'm too hurt at the moment to go there.

I'm not upset with her, but more upset and disappointed with myself. It all makes me feel like I'm...undateable.

Thank you all for hearing me out and offering advice; believe me I took it into account.
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