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Wooing my neighbor: I came. I hugged. I wooed. Now moving on.


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I've not shared a lot of personal stuff here, but figured what the hell. I mentioned this in the iDating thread, but since it's really not an iDate scenario, thought I would throw it out here to the wolves. 

I have a beautiful new neighbor that just moved in a few weeks ago, and I am crushing hard. She's a single (as I've been told from another neighbor) mom of 2 little girls. I'm a single dad of 2, and have my kids the majority of the time, and she appears to have hers most or all of the time as well. We recently discovered that our kids go to the same school. I hadn't realized this because both of her kids are a few years younger than my youngest, so kind of in a different circle of school crew. We have had a few brief exchanges in passing and she seems really sweet.  She (well, her little girl and her) brought me a plate of cookies weekend before last. (Disclaimer: She said the little girl wanted to bring me cookies. She also brought the older couple across the street a plate of cookies, so it wasn't just me... but does this mean she's interested!? Was she just hedging her bets a little by taking the other neighbors cookies?) She has smiled really big and waved every time she has seen me outside. I get the feeling that she's interested, but I'm not 100% sure.

I've made approximately 1,357  trips to the trash can outside to try and make more contact with her. I'm not sure what the next step is. Dating as a single parent SUCKS! I want to get to know her better and would like to ask her out, but I'm not sure how to approach it gracefully. "Hey are you really single?" (kidding) or just say #### it and ask her to lunch (how?)? 

Advice welcomed. 

Shtick encouraged. 

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Helpful links:

  1. pic comparison
  2. a sighting
  3. cooking up BBQ plans
  4. celeb comparison
  5. awwww 
  6. BBQ day confirmed
  7. THE BBQ
  8. playdate report and coffee date set
  9. coffee tolk
  10. breaking news! WWYD?
  11. What did NRJ do?
  12. HugTalk
  13. and then she kissed me
  14. a thank you from NRJ to the FFA
  15. Woo: COMPLETE
  16. it's allllllll over... moving on

 

Edited by Nathan R. Jessep
title update - no help, just woo
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2 minutes ago, Nathan R. Jessep said:

I've not shared a lot of personal stuff here, but figured what the hell. I mentioned this in the iDating thread, but since it's really not an iDate scenario, thought I would throw it out here to the wolves. 

I have a beautiful new neighbor that just moved in a few weeks ago, and I am crushing hard. She's a single (as I've been told from another neighbor) mom of 2 little girls. I'm a single dad of 2, and have my kids the majority of the time, and she appears to have hers most or all of the time as well. We recently discovered that our kids go to the same school. I hadn't realized this because both of her kids are a few years younger than my youngest, so kind of in a different circle of school crew. We have had a few brief exchanges in passing and she seems really sweet.  She (well, her little girl and her) brought me a plate of cookies weekend before last. (Disclaimer: She said the little girl wanted to bring me cookies. She also brought the older couple across the street a plate of cookies, so it wasn't just me... but does this mean she's interested!? Was she just hedging her bets a little by taking the other neighbors cookies?) She has smiled really big and waved every time she has seen me outside. I get the feeling that she's interested, but I'm not 100% sure.

I've made approximately 1,357  trips to the trash can outside to try and make more contact with her. I'm not sure what the next step is. Dating as a single parent SUCKS! I want to get to know her better and would like to ask her out, but I'm not sure how to approach it gracefully. "Hey are you really single?" (kidding) or just say #### it and ask her to lunch (how?)? 

Advice welcomed. 

Shtick encouraged. 

Sum of all bolded = :pickle:

Do it!

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Just now, STBootleg said:

Set up a play date with the children, then you can talk to her all you want.

well, mine are a little older, and so far it has either rained every day or we haven't both been home at the same time, but keeping the possibility open

I did tell her that her kids were welcome to come over to our yard if mine were outside playing

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2 minutes ago, STBootleg said:

Set up a play date with the children, then you can talk to her all you want.

And find a reason to open your wallet and have a magnum condom sticking out

 

and use it. You don't want a Brady Bunch situation happening too soon since you are both fertile

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If they go to the same school, set up a car pool schedule you both can agree on.  Be very helpful in times when making a schedule, but don't agree to everything to be obvious you are wooing her or give her the idea you are the modling type.    This gives you an excuse to talk to her everyday after school. 

Edited by ATC1
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3 minutes ago, DocHolliday said:

Just ask her and her kids over for some dogs and burgers.  Too much thinking about this. 

Considered that too. After all, it would be a neighborly thing to do. But seriously, it has rained all but 2 days in the last 2 weeks. I don't have a covered grilling area. 

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4 minutes ago, ATC1 said:

If they go to the same school, set up a car pool schedule you both can agree on.  Be very helpful in times when making a schedule, but don't agree to everything to be obvious you are wooing her or give her the idea you are the modling type.    This gives you an excuse to talk to her everyday after school. 

Thought about this too, but perhaps a little later in the year.  Her little one just started kindergarten and she mentioned having a rough drop off on Day 1 last Friday.  And not how she would feel about sending her kids with effectively a stranger to her at this point. But filing that one away for later.  

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2 minutes ago, Nathan R. Jessep said:

Thought about this too, but perhaps a little later in the year.  Her little one just started kindergarten and she mentioned having a rough drop off on Day 1 last Friday.  And not how she would feel about sending her kids with effectively a stranger to her at this point. But filing that one away for later.  

Then sleep with her.  You won't be strangers anymore.  

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Next time you see her say:  

"Thanks for the cookies.  Damn, they were so good!  Sweet, moist, and a little nutty -- just how I like my women. 

I'd love to get my hands on your cookies again."

Laugh to kill the awkwardness, but maintain a look that suggests there's some intentional innuendo to what you just said.  Then walk away to let the thought rattle in her head until the next time you see her head.  Shouldn't be long after that next meeting that you too are boning.  Good luck.

 

 

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31 minutes ago, Nathan R. Jessep said:

...

I have a beautiful new neighbor that just moved in a few weeks ago, and I am crushing hard. She's a single (as I've been told from another neighbor) mom of 2 little girls. I'm a single dad of 2, and have my kids the majority of the time, and she appears to have hers most or all of the time as well. We recently discovered that our kids go to the same school. I hadn't realized this because both of her kids are a few years younger than my youngest, so kind of in a different circle of school crew. We have had a few brief exchanges in passing and she seems really sweet.  She (well, her little girl and her) brought me a plate of cookies weekend before last. (Disclaimer: She said the little girl wanted to bring me cookies. She also brought the older couple across the street a plate of cookies, so it wasn't just me... but does this mean she's interested!? Was she just hedging her bets a little by taking the other neighbors cookies?) She has smiled really big and waved every time she has seen me outside. I get the feeling that she's interested, but I'm not 100% sure.

I've made approximately 1,357  trips to the trash can outside to try and make more contact with her. I'm not sure what the next step is. Dating as a single parent SUCKS! I want to get to know her better and would like to ask her out, but I'm not sure how to approach it gracefully. "Hey are you really single?" (kidding) or just say #### it and ask her to lunch (how?)? 

Advice welcomed. 

Shtick encouraged. 

Oh hell yeah. She brought you cookies, man. That is it. Get on it.

What you need to do is go out, hear some great local music, have some awesome food, get drunk, and show her a good time. Get her to laugh, have some fun, and remember what it feels like to be 'not Mom' for a while again. - It is really damned simple.

Have a party, invite some friends over, invite her over. Share some wine. Boom, you're in the zone. If you don't show you're interested she thinks you're not interested. So show you're interested.

Another idea - tell her you made a big meal or have some pie left over and you'd love to have her and the kids over. Whatever, get it going.

Edited by SaintsInDome2006
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21 minutes ago, Nathan R. Jessep said:

Considered that too. After all, it would be a neighborly thing to do. But seriously, it has rained all but 2 days in the last 2 weeks. I don't have a covered grilling area. 

Good luck.  Make a move sooner than later though.  You do not want to be seen as just a neighbor.  If the backyard BBQ goes well, ask her out on a real date. 

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4 minutes ago, Andy Dufresne said:

Say something, you know, grown up...

"We both know dating as a single parent is difficult but would you be interested in having just the first one for now?"

Then recommend sleeping with her just to get it over with and out of the way.  You both have a lot of frustration that needs to get out. 

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54 minutes ago, Nathan R. Jessep said:

I've not shared a lot of personal stuff here, but figured what the hell. I mentioned this in the iDating thread, but since it's really not an iDate scenario, thought I would throw it out here to the wolves. 

I have a beautiful new neighbor that just moved in a few weeks ago, and I am crushing hard. She's a single (as I've been told from another neighbor) mom of 2 little girls. I'm a single dad of 2, and have my kids the majority of the time, and she appears to have hers most or all of the time as well. We recently discovered that our kids go to the same school. I hadn't realized this because both of her kids are a few years younger than my youngest, so kind of in a different circle of school crew. We have had a few brief exchanges in passing and she seems really sweet.  She (well, her little girl and her) brought me a plate of cookies weekend before last. (Disclaimer: She said the little girl wanted to bring me cookies. She also brought the older couple across the street a plate of cookies, so it wasn't just me... but does this mean she's interested!? Was she just hedging her bets a little by taking the other neighbors cookies?) She has smiled really big and waved every time she has seen me outside. I get the feeling that she's interested, but I'm not 100% sure.

I've made approximately 1,357  trips to the trash can outside to try and make more contact with her. I'm not sure what the next step is. Dating as a single parent SUCKS! I want to get to know her better and would like to ask her out, but I'm not sure how to approach it gracefully. "Hey are you really single?" (kidding) or just say #### it and ask her to lunch (how?)? 

Advice welcomed. 

Shtick encouraged. 

Start by having a small neighborhood party and inviting her and the kids, spend time at the party chatting it up with her and go from there.

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WHOLE lotta invitations to the friend zone up in here. Wienies don't get wienie took care of. You don't get over on ladies w responsibilties if you don't put it out there what you really want. Men are complications to them. Good men are complications who help them with their complications. But never let her think it's not what you want until  you're positive it's all you're gonna get and still want the friendship. Then be as much a friend as you were a wooer. Put it away.

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45 minutes ago, DocHolliday said:

Just ask her and her kids over for some dogs and burgers.  Too much thinking about this. 

Pretty much, this. You live next door, she probably wants to make friends / setup a steady bang.

If she shows no interest, you had no chance from the beginning. DocHolliday strikes again.

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45 minutes ago, Nathan R. Jessep said:

Considered that too. After all, it would be a neighborly thing to do. But seriously, it has rained all but 2 days in the last 2 weeks. I don't have a covered grilling area. 

Cover you grilling area

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