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Old 07-15-2018, 07:55 AM
 
80 posts, read 43,883 times
Reputation: 31

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I l am 29/M. I met a 45 year old woman online a couple years ago for a drink. She thought I was too young for her after our first date so there wasn’t a second date.

A couple weeks ago I hit her up to see how she was doing. We started talking and we were going to boating on a lake instead. It rained today so we decided on dinner tomorrow night instead.

She insists it’s not a date but she’s letting me pick her up etc.

Planning on bringing her a bottle of wine when i pick her up, invite myself in when I drop her off and try to escalate.

As far as a plan, that’s all I have lol. It’s worked in the past and hasn’t worked in the past.

Any other tips?
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Old 07-15-2018, 08:02 AM
 
2,483 posts, read 2,475,158 times
Reputation: 3353
Try to relax and be yourself.
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Old 07-15-2018, 08:45 AM
 
1,505 posts, read 1,810,547 times
Reputation: 2748
Are you going on a date or planning a booty call?
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Old 07-15-2018, 09:13 AM
 
14,078 posts, read 16,611,637 times
Reputation: 17654
Quote:
Originally Posted by HereToDate View Post
I l am 29/M. I met a 45 year old woman online a couple years ago for a drink. She thought I was too young for her after our first date so there wasn’t a second date.

A couple weeks ago I hit her up to see how she was doing. We started talking and we were going to boating on a lake instead. It rained today so we decided on dinner tomorrow night instead.

She insists it’s not a date but she’s letting me pick her up etc.

Planning on bringing her a bottle of wine when i pick her up, invite myself in when I drop her off and try to escalate.

As far as a plan, that’s all I have lol. It’s worked in the past and hasn’t worked in the past.

Any other tips?
Tips? Be a gentleman. Don't ask her to split the bill.
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Old 07-15-2018, 09:16 AM
 
Location: The ghetto
17,738 posts, read 9,187,561 times
Reputation: 13327
The bottle of wine seems strange to me.
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Old 07-15-2018, 09:23 AM
 
Location: Pa
42,763 posts, read 52,860,632 times
Reputation: 25362
Good luck! Just be a gentleman and show that you are kind. Lot's of hand,arm,back touching.. ..
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Old 07-15-2018, 09:30 AM
 
Location: Scottsdale, AZ
16,960 posts, read 17,342,198 times
Reputation: 30258
So, you're going just invite yourself in and escalate things with your bottle of wine?

#meetoo story, Lol
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Old 07-15-2018, 09:45 AM
 
Location: Brentwood, Tennessee
49,927 posts, read 59,944,601 times
Reputation: 98359
Yeah dude, don’t “try to escalate.” Gross.

Just go, treat her like a person and not a blow-up doll, and have a good night. Things might end up the way you want anyway if you behave like a human and not a heat-seeking missile.
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Old 07-15-2018, 09:52 AM
 
Location: State of Transition
102,210 posts, read 107,904,670 times
Reputation: 116153
Quote:
Originally Posted by blondiel View Post
Are you going on a date or planning a booty call?
This. This is basically your first date with her, and you're planning to get her soused, push your way into her place after dinner, and use her to end your dry spell? On this "not a date"? Oh, but I guess with the age difference, you're not expecting there to be anything serious with her, anyway? No wonder she thought you were too young, the earlier time.

Whatever.
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Old 07-15-2018, 09:57 AM
 
617 posts, read 1,202,509 times
Reputation: 721
She wasn't into you a few years ago - so she probably isn't into you now. This won't be a good ending.
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