How can I make a move?
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She’s a friend but not one of my best friends. In fact we just hangout when we are with the kids. I don’t estimate her much as she lost my trust since my divorce. (Am not going to share details here. I have nothing against her but she is not a reason to stop me from making a move) she’s 28, and I am 40, so we are not on the same page anyway.
If we would date someday, I think it would be out of town or keeping it secret.
When I was still married I someday asked him if he could help me with insurance matters during a birthday party, because he works for an insurance company. But then some people joined the conversation and it didn’t went further.I Know that kind of look, i can definitely do it. How would you react as a man if I give you that look, knowing that it’s a tricky situation? Isn’t it to straight forward?
Look, you obviously want to go for it and have some kind of situation under the radar. Frankly that sounds like motel hookups out of town. Do you really want that? Wouldn’t you rather just meet available men online?
But if you do, yeah, you’re going to need to be that direct. Asking about insurance or posting topics online is going to be completely ineffective. Touch his hand, give him a look, laugh at his jokes, then ask him if he’s seeing anyone.
“When I was still married I someday asked him if he could help me with insurance matters during a birthday party, because he works for an insurance company. But then some people joined the conversation and it didn’t went further.”
Why would this have gone further? You were married and you asked about insurance.
Your friend actually isn’t a friend, so she’s a non-issue.
I’m sure you can find a time/place where you are in the presence of this man without your exes in the vicinity.
I say don’t do it. Every update you write makes me think this isn’t the move for you. You’re not open to being direct, even though it’ll just take one small but straightforward move to gauge his interest level. And if it has to be a secret? Just enjoy the crush.
Actually though, I could see myself being buzzed and flirty and laughing at a guy and then being like oh can you help me with ~insurance~ and he’d catch my drift. Context matters. In the middle of a normal bland conversation he’s not going to pick up on it.
If you have the patience to wait until you’re both at some birthday party or whatever then I suggest just backing into it:
Hey Joe good to see you. You know I’ve been divorced for two years now, when are you going to ask me to dinner?
If he’s interested he’ll ask you to dinner. If he’s not, he’ll make a nice excuse about not dating his daughter’s friends and you politely excuse yourself to get birthday cake or something.
Hi Leslie, that’s exactly the kind of weird situation I want to avoid. I want to make him know I’m interested but in a more subtle way. I don’t want to make things uncomfortable. I know how to show interest or ask for a date etc… but I’m posting here because I’m looking for a more subtle way to do it…
Okay, but it’s not that weird if someone turns you down politely. It’s not that weird. You’ll see him at birthday parties (maybe) twice a year and maybe make awkward chit chat if he’s not into it?
I am not a man, but essentially, yes I was bold with my husband, twelvish or more years ago. I can be pretty shy, but I go after the guys I like.
Ask him for a drink to talk about insurance, now that you are single. He’ll follow up or he won’t. That’s not bold and sends a point. If he takes you for a drink, you can then tell him you need to be clear, you’re interested in him and maybe tell him what you want if he’s interested. If he’s not interested, says thanks, pay for your drink and your tip and leave. It’s not that awkward.
I realize that didn’t sound super positive, but I say all of this this with encouragement. My husband is 53 this year, is smoking and I’m 39. I fully support this! Good luck!
What 55 year old man is going to be like, oh my god, how disgusting a 40 year old woman is interested in me? If anything, he’ll be complimented even if he’s not interested or seeing someone or whatever.
To be subtle, maybe you could bring him a knife the way he has for you.
All jokes aside, I think this is only as weird as you make it and it doesn’t need to be that weird at all. If he’s not interested, I think you’d move past any awkwardness quickly and resume as normal.
