Search Results: pursuing a younger guy

Should I reach out to him or do you feel it’s awkward and not appropriate?

Yesterday my mom was in town and we went out to a nice restaurant and our waiter was a nice guy who looks like he’s a tad younger than me but we are in our 20s.. he was very nice and he was a nice looking guy.

He was attentive and he told us some of his favorite things on the menu. He did a good job and maybe in the back of my mind I thought he was cute and maybe said it but didn’t really think anything of it.. just a guy doing his job..

He did make eye contact with me even when just talking to my mom.. He did ask questions and asked how I got here since I’m not from this state.. I told him I was an art teacher and I told him how I stopped teaching in December to pursue something else and he tells me he understands completely and he just changed his major in college… did a 180 from film media to production…

I could tell my mom was up to something.. but the conversation was nice and he said he could give us recommendations for things to do and he tried to see if there were any free art tickets to go to the art museum.

My mom embarrassed me and told him I need to meet people and hang out and she ask him for his number and she says “maybe you have friends you can hook her up with “

It’s awkward for me and I tell him that he doesn’t have to do that or feel obligated to and i apologized… it was kind of a pause maybe because it’s awkward but he does say sure and he writes his number down

But I don’t want to reach out because I don’t know if he really wanted to or felt obligated

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?

I like my boss. He is such a sweetheart! He makes eye contact when we talk, laughs/jokes with me, tries to invite me to work outings (which I usually avoid unless they're mandatory), etc. I know he's my boss, but he makes it a point to let me know he'll accept a call for help at any time of the day and wants me to call him when I'm feeling down... I joked about the latter when he first suggested it and accidentally chuckled in a sultry way, which he seemed to do in return? I felt there was some "tension" between us at that time... but that could have been my own "tension" talking.

I love that he's respectful to women regardless of looks, and I also realize that he might not be into me and is just being kind. DGMW, I'm not ugly... but I'm very aware that I'm not everyone's cup of tea... I've been reminded of that multiple times since I was young. Penelope/Colin relationships, especially ones where Pen looks more like Kate or Lady Danbury than Daphne or Queen Charlotte, are uncommon. I've also noticed my coworkers (mostly the women) acting funny towards me ever since this one time he told me he liked my hair. I can't tell when I'm liked because it's so few and far between, so I don't know if they're seeing something I'm not or just being weird... don't men compliment hair?

I made the mistake of dating a coworker while we worked together years ago; I wouldn't dare pursue a relationship with a coworker now. I've also been rejected by every guy I've ever confessed to, so I'm hesitant to put myself out there. I want him to make the first move, but I'm also worried, if he feels the same way, that he's too scared to say anything to me... so I want to try to "guide" him to me. I told him a few months back that I wanted him to "not be a stranger" with me after I quit, and he's said I should let him know when I'm quitting. "Tension" made me feel he was saying it in that sort of way, and I'm thinking of revisiting that convo when I tell him I'm quitting.