Should I and how to ask this man out on a date... Complete wuss.

[singleascheeseslice]

ok, I recently turned 40. I've been single for 8 years - working on myself and trying to get my life back together after an emotionally abusive marriage. I have one DD who is 14.

Even though my life is now somewhat together (lovely little house, decent career, hobbies), I am still around 2 stones overweight. I am working on this. I've used my weight as an excuse not to get out there dating for years but feel like time is passing me by. I spent most of my 30's salvaging the wreckage of my life from my failed marriage, I am now in a new decade and would like to actually enjoy this one! And, create a better life for me and my DD.

Ok backstory out the way. So my DD has been good friends with a lovely girl since they were in primary school. Her friends Dad was a single dad ( widowed) At the time I was only early thirties and he's about 10 years older than me, so didn't look at him in a romantic way at all. He went onto have a relationship with another mum from the school. That recently ended.

I heard from DD that her friend and dad were spending xmas by themselves, they have no other relatives at all. This kind of melted my heart a bit, me and DD are lucky to have my parents and siblings to spend xmas with. Anyway, since then I've been thinking about this man a lot. He is somewhat goodlooking, has a nice nature, is very established in his business, somewhat wealthy and his DD is adorable.

The main problem is that we've never really interacted, aside from waving at the door when DD friend comes around or if I drop DD to their home. I did notice though that at parents evening recently, he did a double take (I'd come from an important meeting so was dressed to kill) which is possibly the only time I've seen any interest from him. I think tbh he is oblivious to the fact that I could be a potential date.

I am wondering if and how I could get on his radar or ask him out myself. I don't know how I would do this, I am a complete wuss, or even if I should? My DD would be happy to spend more time with her friend but I think this would shock her too tbh since its completely out of the blue. I am shocked that I am even considering this myself!

Could you invite him and his daughter over for a Christmas drink/meal..?

Just what i was going to suggest but CoatTails got there first. You could invite the friend over and maybe just say that if her dad will be on his own he could come too.

Oh goodness, this has got me hyperventilating. We haven't ever actually had a conversation, do you think it will seem strange to extend this invite? Would I do it via DD?

I was hoping I'd find him on facebook, add him and like a wuss wait to see if he said hi but alas he isn't on there.

You need to spend some time together in a non-romantic context to see if you actually get on! Agree with inviting the friend over and suggesting he comes too.

Possibly too late now but I'd go for it. Ask him round with his DD. It's quite low stakes because you can pass it off as a play date if it doesn't go well. Don't worry about the weight thing. Not all men like very slender women.

Thanks for the replies! Yes, I need to sort of orchestrate a way to spend time together to see if we even get along. I did just casually ask DD if she thinks we would get along and she thinks he might be too boring (she's a teen though, she thinks most people are boring) and he thinks I am quirky apparently once when I took a while to answer the door when he bought DD home because I was meditating, he said the next time he saw her that your mums quirky isn't she to DD. Not sure if that bodes well or not.

Ok, so I have to somehow get this playdate scenario arranged. I do imagine he's back at work soon though, so I may have missed the boat with the Christmas set-up. I'm overthinking it all I know.

Get a game, something like pandemic. Get the girl over to play it with your DD, then say "that's a better game with four, let's get your dad over"

If he doesn't like board games at Christmas then he's no use at all.

Quirky is an unusual choice of word for someone you've no inerest in. I hinknthat bodes well, as does the fact he was effectively digging with your DD about your personality.

You may find she has told her mate that you were.asking questions about the dad. That is the kind of thing that tends to ping a teen's radar IME. Your secret may not be as safe as you think.... which is not a bad thing at all ;)

oh @Wellthisisunexpected that would be the best possible outcome = him finding out through his DD that I'd been asking after him and then him actually approaching me, if he liked my quirks that is.

Now, I don't know if this is a good idea or not since I've had a couple of Southern Comforts but I just had an idea pop into my head. I could actually hire him to do some work in my house, he is a tradesman and I do need some work doing, omg sounds a bit cheesy now I write it out. But wouldn't that be a good opportunity to actually begin communicating? Ofc, if he already had a hint that I was asking after him it might come across creepy. Lordy, this is a lot more complicated than it was early 20's!!!

Great idea!

Thanks Viv! I have an opportunity tomorrow... my DD is going to a NYE sleep over at her friends' house. The Dad will be home alone listening to 4 teen girls giggle and thud around upstairs for NYE, the poor fella... Although, I'll be home alone at home so that's not that much better .

My new plan is to look gorgeous when I drop her off and ask if he needs a hand. Yet again, sounded better in my head and corny when I type it out but that's the best I've got. Wish me luck!

Even better idea!

Luck!

Yes look gorgeous!!

If he doesn't mention that you look nice you could say something like 'look at me.... all dressed up with nowhere to go '. And then claim friends have cancelled at the last minute.

He will then become gallant and invite you in for drinks.

After a few glasses he will relax and tell you he thinks your hot. And quirky!

You can confess to the white lie later. On your wedding day would be best 😊

Ty ladies, and I wish it had gone so well @beerandpopcorn . I came away thinking it went terrible but in hindsight I learnt some stuff.

So I was looking pretty nice, dropped DD to the door, DD friend answered followed by her dad. DD wished me a happy new year and went off inside with her friend.

I managed some small talk despite never having any small talk with this man ever. I asked if he needed a hand with the sleep over (cringe) and he said, it was cool he had pizza ordered and some ear plugs for later. So I was like oh, great, HNY and already running off up the drive. He then said if I wanted to come in for a drink then I was more than welcome. At which point I felt stupid to go back since I was mid flight but then I'd kick myself if I didn't. So I was like ok, sure and went inside. As we got to the kitchen I saw his EX sat there and was just wtaf at the whole thing. I had a quick coffee and made my excuses and left. As we walked to the door, Dad said in a hushered voice that Ex's DS wanted to come to the sleepover, that's why she was there. They did used to live together, so the DS is like a brother to his DD. All that said, he obviously still has ties and what not to his EX.

I left thinking maybe he does kinda like me because he over-explained that at the doorstep but maybe I was just being used as a pawn in their unfinished business? Eitherway, I think I need to leave that alone and maybe consider OLD in 2019.

So thanks for sharing a tiny snippet of my tragic dating life with me. I have some wine and a cat to see the new year in with lol. Happy New Year x

See what happens op

Haha ofcourse he has ties with ex, they share a daughter :) - he asked you in, so that is good news and you'll have something to talk about next time (pick up?) bring a bottle for the fiest day of the New Year. Have a lovely evening, you're doing great!

I think that the fact that he took time out to explain means he may like you too
..dont give up op !!

Ty ladies, @Poocalypso sorry to explain his DD is from his previous ex wife who passed away around 10 years ago. He then had a relationship with another mum from the school (our DD's school) for around 6 years but that broke up recently. The DS is the new ex's. My DD had informed me that it had ended badly and the dad had spent xmas alone, so I presumed his NY would be alone also. ( I guess you can't depend on teens for information!)

Nah, not negative.

Carry on.

Hmm. I'm still hopeful on this one. Have you been to collect DD yet?

Yes! You are all right, it's not over yet! Another girls parents were there, when I went to collect DD, so I managed to get more small talk in without feeling too awkward. The other mum commented on my weight loss which I couldn't have planned better! He said he spent the night alone with single malt whiskey and the tv so that was reassuring. I wished I'd managed to orchestrate a way to swap numbers, I mean I have most of the other parents numbers incase of anything when they stay over or are out together... that will be the next step!!!