- This topic has 65 replies, 4 voices, and was last updated 6 months, 3 weeks ago by Anonymousse.
LisforLeslieFebruary 28, 2023 at 4:30 pm #1118834
This guy is not a mind reader. And clearly whatever subtle hints you’ve been sending out are not working. So stop playing games.
It’ll be weird only if you make it weird. If he’s like most men, he’ll be flattered. You’re still giving him control but making it clear you’re interested. If he’s interested he’ll make a move. If he’s an immature poopy-head he’ll run away and hide in the bathroom.JessyMarch 1, 2023 at 5:17 am #1118838
Ok, what I understand from your posts is that he might not get the hints (the insurance thing, me looking at him or being intimated..)
Or maybe he got them but is trying to keep the distance because of age gap or his daughter…
I think I will ask him if he is seeing someone next time. But me asking this would not be clear enough as he also asks about my life, how its going etc… I he says he doesn’t see anyone, maybe I could tell him joking, maybe you should try to find yourself a freshly divorced 40 years old blonde woman and ask her out… So if he gets offended, I can says, relax, it was just a joke.
On the other hand, if he laughs and doesn’t respond immediately, at least I will have planted a seed in his mind… And from there he will have to decide whether or not he wants to make a move.
What do you think?LisforLeslieMarch 1, 2023 at 7:36 am #1118839
Sure, that approach might work. But I wouldn’t say “it was a joke” – because it will block any seed you’ve planted. Better to shrug with the implied “your loss, fool” than tell him you’re fucking with him.
I really think you’re over thinking this and trying to twist yourself into knots to make this risk-free. Make some noise! Take a risk!
I’m so confused here, and he’s going to be too. Like what do you actually want? It sounds like you want him to ask you out but then you’d sort of casually date and hook up by sneaking out of town so your ex and his daughter don’t know what’s going on. Ok, I guess, and then would you eventually take it mainstream and be in a legit relationship in public?
Why can’t you just tell him you’d like to get to know him better but this town is so small and gossipy, and would he ever like to get a drink sometime in the next town over? I get that you’re trying to drop a hint that would give you plausible deniability, and sure, you can try that first, but I just think it’s not going to be effective.AnonymousseMarch 1, 2023 at 10:15 am #1118853
He’s a 55 year old man, not a teenager. Ask him out for a drink. Be bold or don’t, there are no ramifications. You’re already divorced. People will always talk in a small town. You can let it bother you or not.
You choose the adventure. I highly doubt he will be offended you are expressing interest. The worst that could happen is he’ll say no and be flattered! I would be flattered if a nice, attractive person 15 years younger than me expressed interest.
What do you want for him, ultimately? Why are you avoiding this question? Is it casual sex? A relationship? Stop worrying what anyone else will think unless it will really affect your life. Will it?
Seriously, what do you want from him? If you want to get to know him better, ask him out for a drink to get to know him better. It doesn’t have to be some huge sexual come on. You can have a drink, be one on one with him and maybe something Will Burt’s inside you both and maybe you’ll realize he has terrible breath and old school selfish misogynistic tendencies that lead him to be single. You never know.
Go forth into the wild beyond of asking him for a simple drink, or not. It’s not a huge deal if he says no. It won’t crush you socially.AnonymousseMarch 1, 2023 at 10:16 am #1118855
At our age (I’m 39) hints are not cute, IMO. It’s immature.
Ask him out and stop this hinting. What hinting have you given, by the way? Asking him about insurance when you were married was not flirting.
You’re overthinking this way too much.
While reading, my first thought was that if he was interested, he would have done something about it already. Your excuse was that your ex was around so he couldn’t. That doesn’t hold water. He can get a hold of you and ask you out other ways, like social media or getting your number.
Honestly, as List and Anon said, I’d take a more direct approach.
But before you do that, you need to decide how’d you want something to go down, as Kate mentioned, then proceed accordingly.
You’re acting like a high schooler right now.
Asking about insurance when you were married, looking at him, and “being intimidated” — whatever that means — are not hints that you are interested! Neither is posting something about fitness on social media hoping he’ll somehow know you posted to all your friends just for him. You are 40 and you say you’ve dated quite a bit, but it really doesn’t sound like it IMO.
I don’t understand why this is such a big deal, LW. His daughter isn’t really your friend since you don’t trust or like her and it seems to me in a small town, your ex husband would know anyone you date. Not to mention, I’ve heard anecdotally, having never lived in a small town myself, is that it’s pretty normal in areas with a limited pool of singles for everyone to kinda date everyone. I don’t get it.JessyMarch 1, 2023 at 10:52 am #1118862
The hints I gave him: essentially the insurance stuff. I told him I was considering taking a retirement insurance and told him maybe you can help me on it, do the follow up. But he never did. Also I look at him a lot haha… and once I complimented him on his weight loss, I told him he was looking good.
What I want is to know him better. Going out for a drink, talk together and see wether my opinion of him is the right one (but I already know much about him, his life, so…) And if we enjoy each other I want something casual first and then see how it develops. When I say casual, I mean not committed. At this point of the relationship, we would keep it secret and if someday it turns out to become serious then we will see.
But I’m still very concerned about how my ex would react and all the people we know. My ex always told me to find someone he doesn’t know yet, (meaning out of town because he knows everybody). I had two affairs last year with guys from my town. They were younger, one was 25 and the other 30, and he knew about it because people talk. And he didn’t like it at all and said that now everyone knows I’m looking for younger boys. Even my dad’s friend knows theses guys and my friend surely told him about them, at least I guess… Because once he asked me how my “little life” was going, it was one year after my divorce, that time I was dating multiple guys on the same time, and going out with them in town sometimes… (which was a bad idea btw)
I have to figure out whether I’m willing to take that risk or not. But I think I will. After all, I’m divorced, I’m a big girl and I am free to do what ever I want… Don’t you think? What Im afraid of is him saying he is not interested and all the others knowing what I did and judge me for it… When I say all the others, I mean, the waiters/customers from the bar, then his family, then my friend, my ex and all of my ex’s buddies… and to go even further the entire town haha. I would feel so ashamed.JessyMarch 1, 2023 at 10:59 am #1118865
“While reading, my first thought was that if he was interested, he would have done something about it already. Your excuse was that your ex was around so he couldn’t. That doesn’t hold water. He can get a hold of you and ask you out other ways, like social media or getting your number.”
I also think he could have done something… but then I think of the consequences of him asking his daughters friend out and I think he would never do it even if he was interested… He is a really protective dad and trying to rekindle their relationship as he hasn’t been very present during her childhood because he left.
I’m not acting like a high schooler, I’m just being cautious and trying to find the best approach if there is one… This is being an adult.
“The hints I gave him: essentially the insurance stuff. I told him I was considering taking a retirement insurance and told him maybe you can help me on it, do the follow up. But he never did. Also I look at him a lot haha… and once I complimented him on his weight loss, I told him he was looking good.”
These are not hints. These are normal things people do and say. I compliment people all the time, males and females.