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Search Results: flirting with older women
What does "the guy who likes to watch" actually want from a woman?
I tell a guy I love to dance and he starts to whine about how his dancing days are over. I ask "really"? and start teasing him about it bc he's physically fit and very sporty, so this seems odd. I tell him that it's too...
How to slow down without hitting the breaks on a new flirtatious association?
I just met a guy (a few years older, nothing crazy). Seems nice. He approached me... which I like. Has good gentlemanly manners... which I like. He works in an industry I understand... which is good, so we can talk shop...
When a younger guy propositions an older woman, is it "just for fun" by default?
I've had this dialogue with a few people bc in my opinion a younger guy with his whole life ahead of him isn't propositioning a woman old enough to be his mother for anything more than a short-term fling. He wants to say...
How do I cope with lifelong loneliness and never having a relationship?
Im in my late 20s and long story short; never had a boyfriend or even dated. I never had friends. I never had a relationship with my family. Every social interaction goes horribly wrong whether i speak or not so i can't...
77five
Xper 5 Age: 27 Is my affectionate male friend straight or secretly crushing on my bi best friend?
My male best friend is bisexual, and we have a mutual male friend from the improv community. This guy has more female friends than male friends. He talks to women naturally, but with men he seems unable to start a...
Anonymous
(25-29) Why do younger women seem to hate on men in their mid-30s?
I can't always tell how old a female is these days. Was flirting with one in maybe her mid twenties im 36. Then all these other girls hopped on facebook and were like dude what are you 40? Man... first time I ever got...
red324
Guru Age: 37 Is my 59-year-old married coworker actually flirting or just being friendly?
I am asking mysel about the behaviour of a female coworker of mine. As a general presentation, it is a 59-year-old woman, married. When we walk in the hallways or in the yard, if she sees a colleague from a distance, she...
Plutarh
Xper 1 Age: 43 Is my sister’s older boyfriend still a pimp and should I be worried?
My sister is dating a guy way older than her, She told me that he use to pimp in the 70s. He moved to Atlanta in the early 2000s and he was a landlord and helped young woman to get a place to stay, he never mentioned men....
Anonymous
(30-35) OK, this is getting out of hand. So apparently I can’t talk to a girl legally now?
Sorry for being repetitive, but this is the second girl at work that went to HR about me. I am 48 years old. I am autistic male who never dated a girl and is looking for a girlfriend. However, this girl, I had no interest...
Dbman99
Xper 2 Age: 48 Meeting older women on walks with dogs?
Hello, I (30 yo) am meeting one older women (roughly 50 yo) when I walk with dogs. She is single. I am curious if she is flirting with me or she is just friendly. Some info: when we first met. She “stopped...
threeguy123
Xper 1 Age: 31 I am still a virgin at 28, what am I doing so wrong?
I have been working out for some time. I recently finally got a 6-pack even though it wasn’t easy in the slightest. I am still a virgin at 28M though. I usually go for women who look about what others say I am on a...
Anonymous
(25-29) 52 year old M and 39 year old F, can it work?
Hi All, I've just turned 52. I've been single for a while as a separation in my 40's was such a nightmare I thought I didn't want to go through that again. Now those years have been good, I did a lot of things I...
Anonymous
(45 Plus) Is it more OK, common these days with age gaps?
When I was young in my late teens. 20s it happened that older guys that were close to my dads age would flirt with me (which I found odd and not into). Now in my 40s it has happened that guys that could be close in age if...
Noredcarpet
Xper 5 Age: 46 What the F*ck is “Rizzing”?
Aaaaaaaaaaand ladies and gentlemen, we have a nother reason why social media is garbage that is bad for you. It’s called “rizzing.” And what the fuck exactly is “rizzing”? “Rizzing” is a stupid-sounding modern day...
So I am right this is leading someone on?
I worked with a woman and yeah I know she isn’t interested my buddy says she just wanted to have a conversation. I reply with I rather not and it’s a waste of time because so many of them just flirt lead you on then play...
Anonymous
(25-29) Is an older woman flirting if she rubs my foot w hers under the table and says reconsidering your career choice about a OF rumour?
She also said w legs like that surely you’re not leaving ….:/
Anonymous
(25-29) How do I know if he likes me back? Are these signs that he is interested?
I get butterflies every time I am around him and its hard for me to talk to him. Well we speak a little sometimes I feel I might be annoying to him simply because I am hyper and a bit loud but I enjoy making people all...
Anonymous
(30-35) 
Nahid1707
Guru Age: 27 Should I give this cheater a 2nd chance?
Turns out I’m banned from Reddit, so here I am I guess. I lost my virginity as old as 33, girlfriend who took it cheated all the time and I was lucky to get action even once every week from her (usually less). I took...
Anonymous
(25-29) Is it normal for a 30 year old woman to flirt with a 24 year old guy?
So I'm 24 years old and at my new-ish job there's this 30 year old woman who's been flirting with me, or at least I think. She's very affectionate and gives me a lot of compliments, including a lot based on my physical...
Anonymous
(18-24) 