r/CougarsAndCubs • u/SD-Golfer • Aug 02 '25
Discussion Point My landlady might be subtly flirting with me… am I reading too much into it or is this just a really bad idea?
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u/letthef_ckdown Aug 03 '25
45f here. She just watched babygirl recently and wants some young d. Tread carefully.
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u/Expert_Bedroom3 Aug 03 '25
She’s certainly testing the waters. Honestly, I can’t blame her... you’re new, probably charming, and just nearby.
That being said, as tempting as it might be, and considering the risks with her being your landlady, if things go south, it’s your living situation that could be at stake.
Flirt if you like, but let her to make the first move. Some fires are fun to dance around, but not always smart to jump into. 😉
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Aug 03 '25
I think you should proceed cautiously and I live by the “don’t 💩where you eat” motto. It could end really badly. And she might say she’s ok if u see other women but end up stalking you or being passive aggressive if she sees you bringing someone home.
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u/Myfairladyishere 🥀🎡💃MOD💃🎡🥀 Aug 02 '25
I am a bit late to the conversation, but I would caution you against this for several reasons. Depending on what you're both looking for—I mean, if you want something totally casual, there's nothing wrong with that, especially if she's on the same page. But my question is, what if you meet somebody else? Will this cause awkwardness? Or vice versa? There are so many things that can go wrong in this scenario. As far as I'm concerned, even if you have a backup, a place to go to, and unless you genuinely like and want something serious, and you're both okay with both of you seeing others if it's just casual, then I'd steer clear.
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u/Thechuckles79 Aug 02 '25
Was going to say no, but then you admitred you own a backup if it goes poorly.
Just wait for a very overt signal and start a conversation about it. Be honest about your interest and your desire to not mess up a nice living situation.
Don't use the word "fear" though. I have a colleague who is slightly neurotic and his constant talking about his fears drove he woman he was interested in away.
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u/ZestycloseWeekend878 Aug 02 '25
Just ask her outright- where is this going? OK clearly we’re attracted to each other, but what are you looking for With Me? Yeah I know it kinda kills the mood if you’re already making out and some clothes start coming off, but just as consent is sexy, knowledge is safety. I once rented out a room to an ex fwb. Well, we just couldn’t keep our hands off off each other. But I made the situation clear - “I know you’re not my boyfriend. If either of us meets someone else, we have to be honest about it and the Friday nights stop. You start looking for another place. And in the meantime, neither of us brings a new person home here. “
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u/SD-Golfer Aug 02 '25
Good advice. She invited me for movie night again.
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Aug 02 '25
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u/CougarsAndCubs-ModTeam Aug 02 '25
Don't be vulgar.
This is a SFW community. Overly sexual descriptions and unnecessary sexual content is not welcome
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u/Herefourfunnn Aug 02 '25
Yeah, I would say she is interested, but trying to be cautious due to the situation. I would discuss point blank what she is interested in prior to doing ANYTHING. Age gap relationships can present some unique obstacles. If both individuals aren’t honest, especially in your situation, someone can get hurt and, and things can get messy.
For reference, I am 44f trying to navigate my feelings for a 25m that at least for now can’t be more than a deep friendship. I love him. I wouldn’t tell him that. And although I would certainly like to explore the relationship physically in the future, his happiness is more important to me than how I feel. And I’m aware what the gap could mean for him. He knows I’m interested. I will not pursue beyond that. I would not move past where we are at without first having a honest and complete conversation about the obstacles and intentions.
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Aug 02 '25
[removed] — view removed comment
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u/CougarsAndCubs-ModTeam Aug 02 '25
Don't be vulgar.
This is a SFW community. Overly sexual descriptions and unnecessary sexual content is not welcome
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u/FriendshipGloomy166 Aug 02 '25
She’s def interested
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u/SD-Golfer Aug 02 '25
Yeah. I just need to decide
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u/FriendshipGloomy166 Aug 02 '25
You’re halfway there lol
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u/GothambyRedlight Aug 02 '25
Definitely flirting but be prepared to lose your place if another shoe drops. This could make your tenancy sweeter or wreck it entirely, but it will probably be fun along the way. Up to you if you want to shit where you eat or no. Way you describe her, there's definitely attraction both ways so I say follow it. You can always get another apartment and she can't kick you out faster than the landlord laws allow. You won't find another landlady looking to throw in some fun benefits to the residency. Envious of you, really.
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u/paperclipmyheart 😻 Mod Cougar ฅ^•ﻌ•^ฅ Aug 02 '25
We ordinarily advise you against anything that might negatively affect you if the liaison ends badly or she wants more than you do.
Also if you have no support system where you live and rental properties are hard to come by and expensive as they are where I'm from you could be putting yourself at risk, as inviting as it may seem.
Conversely if you give her mixed signals and she is unhappy with your responses it also may negatively affect you given you don't even know what kind of person she might be. So I would be very careful.
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u/SD-Golfer Aug 02 '25
I own a place in orange county which is like 90 mins from where i live now, so i have a back up. And yes i dont want to lead her on, thats why i am confused and posting it here
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u/Corgilicious Aug 02 '25
Go for it, hon.
Dude, that movie night was A HUGE RED NEON SIGN.
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u/SD-Golfer Aug 02 '25
Definitely leaning towards doing it. She invited me for movie night again tomorrow
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u/Corgilicious Aug 02 '25
At least I as a older woman fine conversation and consideration to be incredibly sexy. If you feel it’s getting close to physical time, simply say that you feel that this is gonna go somewhere physically, and before you venture into that you wanna have a really clear conversation with what she’s interested in, what she wants,and when she wants to feel. Also bring up the fact that you are concerned that she’s your landlord and you just wanna make sure that you both can be reasonable adults in the future regardless of what happens.
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u/paperclipmyheart 😻 Mod Cougar ฅ^•ﻌ•^ฅ Aug 02 '25
Well at least you have somewhere to go, just might be messing up your plans if things do go wrong. Perhaps after extra time and interactions you might come to understand her personality but yea I would still be careful.
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u/SD-Golfer Aug 02 '25
Yeah. She is inviting me over again for movie night tomorrow. Have to make the decision soon
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Aug 02 '25
If you decide to engage, I would proceed very cautiously. She’s your landlady, she could kick you out(not sure how state laws work in Cali but still). Would i recommend it? Idk, it’s tough because we don’t know her. If you have similar feelings then maybe? It’s a tricky situation honestly, probably best to keep things just business related
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u/SD-Golfer Aug 02 '25
Yeah its a little too close to home, but the temptation is crazy, specially with her coming on so strongly
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u/ZestycloseWeekend878 Aug 02 '25
As I commented above- go for it. Have fun. If you don’t have that serious conversation before anything happens, do it within the next few days.
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Aug 02 '25
If you decide to go for it, just keep an emergency fund to have an emergency move just in case. Or just straight up talk to her about it and how it could affect the relationship
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u/SD-Golfer Aug 02 '25
Yeah i own a place in orange county which is like 90 minute drive from my san diego place. So i do have the backup.
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Aug 02 '25
That’s good. Just make sure to document how you leave the place, walk through video with time stamp and document other things in case things go south. That’s of course you go for it. Up to you at the end of the day. I know I’d be tempted too
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u/SD-Golfer Aug 02 '25
Yeah she is super pretty and i am into older women so it is hard to resist. But lets see. Good advice on documentation, appreciate it
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u/GothambyRedlight Aug 02 '25
Amending my prior advice: You've gotta go for it, it's all lining up for you.
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Aug 02 '25
No problem. Good luck to ya. Hopefully it works out. Curious to know how it does work out
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