Dating older women

[Lacoste44]

Hey guy's

This weekend a lady from work and I went for a road trip to one of her friends place and stayed the night. I am 24 and shes 41. We get along great with each other and in no ways do I feel like she treats me like a kid. We joke and flirt all the time together and I always throw in the older age comments for fun and she laughs along. She doesn't look like she's 41 and I try to look past her age anyways, I look for the enjoyment that we share together. At work sometimes I don't see her all day and then other days I may see here for 5 minutes or so. We have worked together for 4 years and she has dated 1 guy in those 4 years and he was a loser, when I met him.

I have a huge crush on her and it's like we were meant to be together but our ages are 17 years apart. She has a 15 year old kid and a 21 year old who doesn't live at home. She has been married twice but I think it's the guy's loss. She's a great person and I enjoy being around her and think about her all the time sometimes. The thing is I don't know if she would even consider dating someone 17 years younger then her and is this is just a fun thing for her or a friendship thing. I like the mature age thing about her, compared to girls my age and the fact that she is happy with her self and she seams to enjoy being around me. She doesn't buy me stuff and it's not like she's looking for that one night stand. She even let me drive her car this weekend which kind of showed me that she trusted me. If she didn't like me I am sure she wouldn't invited me this weekend to come along with her. She like to classify her self as a cougar but I don't really see it that.


I just don't know how to approach asking her out and if she would even be willing to go on a date with me.

 

[Brian]

Dude, if she's a self-proclaimed cougar, go for it!

You should just do it. Ask her out or approach the subject how you see fit, but do it.

 

[kevin_d'_lion]

She doesn't buy me stuff and it's not like she's looking for that one night stand. She even let me drive her car this weekend which kind of showed me that she trusted me. If she didn't like me I am sure she wouldn't invited me this weekend to come along with her. She like to classify her self as a cougar but I don't really see it that.


I just don't know how to approach asking her out and if she would even be willing to go on a date with me.

Seems you've already started the act of dating the way she invited you to come along with her on weekend, and like she let you drive her car, and talk about personal things in her life.

I don't find any differences about age. It really doesn't matter as long as you both agree and meet on the same level. Well, there's no reason why shouldn't approach her about it. Go ahead, tell her straight in a casual way like the usual conversation you are doing to her. She'll go on a date with you. I'm pretty sure.

 

[cheaptrickfan]

I can give you a 41 year-old woman's perspective.

The thing is I don't know if she would even consider dating someone 17 years younger then her and is this is just a fun thing for her or a friendship thing.

You've actually answered it right here:

She like to classify her self as a cougar but I don't really see it that.

If she refers to herself as a cougar, that right there tells me that an age difference doesn't concern her.

Now the question is which younger guy, and judging by your post, the fact that she hangs out with you, jokes and flirts, and most importantly, took you on a road trip with her leads me to think that you have a shot.

I'd say that signs are good.

I just don't know how to approach asking her out and if she would even be willing to go on a date with me.

I say just go on ahead and ask her out on a date.

Good luck!

 

[EveWasFramed]

Another 41 year old woman chimes in....


lol, I'd do it. As long as the guy could keep up with my maturity level (at least for the most part), I'd date a guy your age.

 

[nerdygirl]

It kind of sounds like you guys are already dating, but nobody has given it that title. The age difference between two adults is only important between them, and it seems like you're both fine with it.

 

[Twitchy]

I'd agree that it sounds like you're already dating this person.

The most successful relationship I ever had was with someone five years older. It's not as large a gap as 17 years, but I see no reason why that couldn't work just as well (or better).

People put too much emphasis on age anyway.

good luck...

 

[Haz]

That's wonderful I've always appreciated the company of older women, all of my sexual relationships have been with women almost twice my age.

Just go with the flow.... don't build her up to be "the one" as this can be the biggest mistake you ever make with anyone you fancy. I would just suggest saying to her "Can I talk to you about something?", at a private moment and let her know that you find you her attractive and you have feelings for her. At the very least, if she makes it clear she doesn't want to progress anywhere with it she is sure to be flattered. If it wasn't to be it wasn't to be.... sounds like you have a good shot though.

Keep in mind most self described cougars aren't looking for a relationship, young men full of hormones are mostly only appealing for one thing. The age gap almost always makes a relationship impractical, I only say this because i'm sure there are exceptions but I doubt there are many. You gotta watch out for roping in the whole broken down alcohol emotional wreck you didn't expect as well, there is nothing worse than drunken phone calls begging you to come over at 3 am for a crying session about an ex-husband and the kid getting into drugs followed by lousy sex. This is the sad truth of the fantasy, sometimes.

 

[TheWickedOne]

Another 41 year old woman adds to the list:

GO FOR IT!

 

[EveWasFramed]

lmao, I had no idea there were so many of us....

 

[cheaptrickfan]

lmao, I had no idea there were so many of us....

I think we're a special subset of "lonely." It's funny in an odd way, but then again everything is striking me as absurdly, inappropriately funny lately.

 

[mintymint]

my maturity level

...There was one!?

---

I don't see a problem with an age difference like that unless you planned of having baby time However, you won't know how serious of a thing she wants until you go ahead and ask her. Also, women live longer, so the number of years that each of you has left until you theoretically die is closer than your age difference... if that helps to mentally bridge the divide

 

[Lacoste44]

Thanks for the support. Do you think this would have any effect on our work relationship. I was just thinking if I had her private for a second and I just asked her if she would like to go for dinner sometime, doesn't have to be a date just be like friends going out for dinner. What about her 21 year old kid that doesn't live at home, would this have any effect?

 

[Haz]

I'd cut directly to the point as soon as possible, she has been around and this dating thing might just seem silly to her. You've already spent time getting to know her.... just let her know how you feel and do it in a respectful way. It won't affect your work relationship unless you aren't willing to handle that she may potentially refuse your advances, if you can accept this with good cheer you can still remain friends and keep a professional relationship.

The whole "I have a daughter or son who is your age" thing has come up a few times in my experience, if this causes discomfort for her (and it probably will) there is little that can be done.

 

[Brian]

For what it's worth to the other, single 40ish year old women in this thread, I too am totally down with the cougar thing.

 

[Lonesome Crow]

This is totLLY messed up !!!!
Don't you all know how difficult it is to find a single woman my own age without babies living at home.
Now, i have to compete with the young guns....
Errr..wtf !!!!....I guess I'm just going to have to start hitting on younger women.
Just feels weird to be slapp'in her ass say'in "who's ur daddy!"
when I'm actaully old enough to be her daddy.

I guess I'm just going to have to get over it and deal with it.

but it would probably really mess with my duaghters to be calling a woman of dream "MOM" when she's younger than them.

 

[EveWasFramed]

This is totLLY messed up !!!!
Don't you all know how difficult it is to find a single woman my own age without babies living at home.
Now, i have to compete with the young guns....

lmfao, LC!

 

[Lacoste44]

So were planning on going to the movies, she said just random when another co-worker and I was around I would like to go see this show and I am like I am in. Other co-worker didn't get a chance to say anything. So just planned for the two of us. Should I mention I like her on the way and would like to continue to see her, or if she would be willing to date me.

 

[Brian]

So were planning on going to the movies, she said just random when another co-worker and I was around I would like to go see this show and I am like I am in. Other co-worker didn't get a chance to say anything. So just planned for the two of us. Should I mention I like her on the way and would like to continue to see her, or if she would be willing to date me.

After. Do it after. Just be like "So...I kind of like you"

Or something.

 

[Lacoste44]

Question guys. This morning she said she had to cancel movie cause of her kids doing something. So I said no worries not a big deal and she said she would go next week or something. Later that day I planned to go on a weekend away thing with a buddy from work and just joking said don't worry won't cheat on you and then she said ah don't worry there is ton of younger girls out there for you. So what does this mean, it just made my somewhat said through the whole day because I have such strong feelings for her and think about her often not for the in bed part either.