Search Results: old friend

He said months ago that he doesn’t reciprocate my feelings, but recently started flirting back, then backing off, then flirting back…. It’s really messing with my head and I feel like I’m going insane… it needs to stop. Doesn’t help that he’ll cheer me up when I’m down either.
And he’ll respond well to my sexual flirting or carry on conversations about sex… and he’ll be clearly enjoying it, like smiling and blushing and he even once got hard around me…. I dunno… it’s just too much.

do I send him a message saying it’s best we don’t talk anymore? Do I just gradually pull away? What do I do?
also he’s much older than me. I should’ve stopped it a year ago. Weird thing is that he never followed me back on instagram, but he follows everyone else back… but he would sometimes comment on my Facebook posts..

Me and my friend have had similar age preferences for years and that was to stick to men our age. I’m 40, she’s 39. People have been telling us for years to date men who were several years older than us. This includes our parents, aunts and uncles, each other’s parents, family friends, church members, etc. she’s even had friends our own age tell her that she should be dating older men (or so she says). I decided to give it try last spring after my same age boyfriend who had two kids and massive debt dumped me for being “too good” for him (I supported his broke ass financially), and I can say my luck changed drastically. Current guy is 55 years old and we both agreed we’re stuck with each other. At the end of summer, I had a party and invited my friend (recently heartbroken about being dumped but a guy our age for a younger girl), my boyfriend, all of his friends and all of their wives LOVED her. Every one of them and myself all thought she was perfect for a friend of theirs who was looking for someone just like her, so we agree to try to fix them up (the friend had met her once before at a charity event we were working). BF’s friend is also 55, retired, financially secure, gets a pension every month, good Christian, still works part time, has his house paid off and is looking for a woman to spoil rotten. So we pitch the idea to his friend, and the friend’s response is “that girl is a catch! She’s a nice girl with a good heart, she’s doing something with her life and she’s ABSOLUTELY BEAUTIFUL! Yes, please fix me up with her.” I mention it to her and try to convince her to no avail, she won’t date him just because he’s 16 years older than her. I told her she needs to be dating men in their 50’s and early 60’s, not our age. She said NEVER. I told her then that she’s a stubborn asshole who’s throwing away a good guy. Opinions? I want to show this to her to make her realize this is true. Women have been marrying older men for years so it clearly works.

When it comes to dating and relationships, who has it more difficult, who struggles more:

- Mark has gone out on several dates already and has no problems making friends nor talking to people. However, he seems unable to turn a date into a girlfriend, can't make it past friendship.

- Susy is getting older, will be 32 soon and this is the 3rd boyfriend she can't get a proposal, marriage and kids. She's unable to get out of the girlfriendzone. She wants to be a wife and mother.