Search Results: relationship with an old friend

I have this guy in my class whom I’ve known for a long time from an old school. We both moved to the same college, and since we didn’t know anyone there, we naturally started talking more. Recently, as we’ve been spending more one-on-one time together, I’ve started developing feelings for him.

I’ve heard that most guys believe men and women can’t really be just friends, so I thought that by spending more time together and getting closer, maybe he’d start to like me too. I consider myself an attractive person—people tend to turn their heads when I enter a room—so I wonder if he sees me as just a friend or if he might want something more.

The only thing that makes me doubt is that I’m four years older than him, and I wonder if that affects how he sees me. One thing I’m sure about is that if he wanted a hookup, he wouldn’t say no—but I’m not sure if he would actually want a relationship with me.

In December 2024, I met a guy on an app and was instantly attracted to him. He expressed that he found me pretty, which made me feel special. Despite the age difference of 1 year and 10 months—me being older—I didn’t think it would lead anywhere serious. However, I was pleasantly surprised when we began talking every single day. He would text me at any moment, even while he was at school or at practice, sharing pictures of what he was doing. Our conversations often stretched late into the night, sometimes until 1:00 AM, and he consistently sent me good morning texts that brightened my day.

As our connection deepened over the months, I noticed that he was genuinely invested in my life, asking about my family and recommending places he thought I’d enjoy. His enthusiasm is evident in his texting style; he often double, triple, and even quadruple texts, which shows how much he enjoys communicating with me. However, about six months in, while he was on vacation, his good morning texts stopped, although he still reached out regularly.

Now, nearly a year into our relationship, I’m left wondering why he hasn’t asked me out. It feels like we have a strong bond, akin to a romantic relationship, yet there’s no official label. He has shown signs of jealousy when I mentioned dating someone else, which makes me think he has deeper feelings for me. Despite our closeness, I’m unsure if he sees me as just a close friend or if he’s hesitating to take the next step. Our dynamic is unique, filled with warmth and connection, but I can’t help but wonder what’s holding him back from making a move.

I’m 40, she’s 39 and both of us spent way too much time navigating the dating world. We’ve both been told since turning 30 to date men 10 to 20 years older. I’ve been more open to it than she was. She’s still not open to it. She’s really pretty so her looks aren’t an issue, but she gets passed over and dumped CONSTANTLY by men our age for younger women and the last time really hurt her.

I started dating a man age 54 last year and have never been happier, and dating him taught me two things: 1.) it’s really true that men like to be a little bit older than their women and 2.) men need to feel lucky to have a woman in order for a relationship to work (my boyfriend and I both know how lucky we are to have each other, but he courted and pursued me like no man my own age ever did). My friend has not accepted this yet, and it’s such a shame because my boyfriend has a friend who is perfect for her. The guy met her one time and has been begging me ever since to set him up with her and he’s been pursuing her nonstop but she won’t give him a chance just because he’s 60. She says the age gap is too big and she won’t date him because he’s 20 years older even though he treats women really well, can give her the life and love she deserves and can also respect all of the wonderful qualities that she has to offer.

That man has outright told me that he wants someone our age. How can I make her see that women our age are better off with men that age?

She said the oldest she’ll date is 50.

Am I right when I say middle aged women in their late 30’s should be dating men in their late 50’s/early 60’s? Is she right that the age gap is too big?