Search Results: dating an older guy relationship

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?

30F either DA or FA, want to say I’m some kind of avoidant. Based on life experiences, are these pretty tell tale signs I’m probably…well not attractive? I’ve always questioned how almost every pretty woman I’ve come across is always in a relationship with an equally attractive guy. When I was chubby younger, I thought losing weight would solve everything and it hasn’t. I feel like regardless of what anyone else says, I’ll always wholeheartedly believe attractive women have no issue finding a partner & they have life easier. I’ve been told I’m attractive by a variety of people for most of my life, even when I was chubby. I’m not thin, 5’7 women’s US 10 so midsize but I have that thicker thigh/flatter stomach build. The only time I get attention from guys I find attractive are on dating apps and that’s not telling in my opinion. I’ve been told this guy looked at me/this guy found me attractive from other people but the guy never makes it known to me. And there’s been very very few times where I would see an attractive guy making eye contact with me or at least caught my gaze but I just look away b/c I don’t see the point. I’m anxious/reserved but a lot of people with anxiety are in fulfilling relationships.

Last thing I’ll add was being bullied pretty badly as a kid, again I was chubby so I know this played a part. Worse in middle school, I didn’t have to be homeschooled but it still sucked really freaking bad. And in HS but not as extreme as middle school, HS was more mean girls if anything. As an adult at old jobs, I did have confrontation/clashing w/personalities too. And let’s not forget shit bosses. Since I’ve worked remotely for the past few years, I haven’t had drama with coworkers or mgmt. Let’s hope it stays that way, I’ve had to deal with toxic family members too but that’s a thing of the past.

I’M SO CONVINCED THESE THINGS DON’T HAPPEN TO ATTRACTIVE PEOPLE