Search Results: ask him casually

I briefly dated a guy (about a month). He let me know he didn't feel the spark he was looking for. He said he loved spending time together and would love to be friends. I can see how we are not a good fit based on a couple of red flags I saw. I would like to ask him to casually sleep together. Any advice? And have you ever turned down a friends with benefits situation and why?

I have two friends: both are 40, have chosen the single life for years. One is a guy, he was friends with a girl in her early 30’s for a year and dated her casually for a year before he finally decided she was the one and asked her to be his girlfriend. After one year of seriously dating, he proposed marriage at Christmas. They married two months later. He’s a guy, we’ll call him Ryan. Him taking his time is fine.

The other friend is a woman (we’ll call her Tara), she’s been “seeing” a guy (also 40) for at least 9 months. They haven’t labeled it yet, every time I ask her when she’s labeling the relationship she always says “we’re taking our time with it, keeping it casual and just being friends first”. I love Tara, but she’s out of her freakin mind. I demanded my boyfriend to define the relationship after 5 months. Tara does want this guy, but she just lives in her own little shell and won’t demand what she wants. She just sits back lets things happen and says she wants him to define it in his own time (I told her drop his ass if he doesn’t define it at the end of this month).

It’s fine that Ryan took his time. He’s a guy and it’s more socially accepted for him to put off relationships and marriage. For women I don’t understand it though. I feel like when we go that route, we get used, we get our time wasted and we get hurt. I think Tara is making a huge mistake, but my boyfriend says she’s not. What if she defines the relationship and then decides she doesn’t like him after all (that’s his logic). Maybe because I’m also dying to matchmake her and there’s a friend of my bf’s who I want her to meet (because he’s dying to date her and I think they’re perfect for each other).