Okay, I'm 20 and there's this woman that comes into my work all the time that's about 25, so she's older than I am. We've had talks many times and I know a lot about her, but over the last few months it seems like she's dropping me hints and making some comments that make me think that she wants to sleep with me. I don't think it's starting a relationship or anything, I think she truly wants to have sex with me. Now this woman is really good looking and the truth is I want to have sex with her too.
Here's where the problem comes in. True she's older, but she's also a single mom. She has a son I know, and I'm not sure how I should approach this now. I mean, truth be told, I've been rather shy about this, since I've never actually had sex before or even had a girlfriend, so I haven't really thrown any advances back at her. This is tough, because I really really want to sleep with her. She's a lot of fun and I like her, but I also don't want to have a relationship with her, obviously, because she's a mother and I'm too young to deal with that. So I'm nervous approaching that. Then there's most of me that believes that she's coming on to me (and is quite convinced) but then there's a teeny percent of me that thinks maybe it's all in my head.
Of course, if I ever did anything, I'd be safe about it and use a condom. So how do you think I should handle this? I mean, we're both adults and all, but is it right? I know she's a mom and all, but I'm really hot for her and I'd also like to have my first experiance sometime soon.
Also, if i do decide to go for it, how should I approach the situation and how can I verify if she really is making sexual advances or if it's all my imagination?
Thanks for the advice.


Ok listen theres only one way to find out if she really likes you talk to her about try not to be shy or nervous because if she says yeah then you get what you want and if she says no you no worse of then you would have been if youd never asked her so invite her out somewhere thats casual and not too romantic or shell think you want a relationship try a group thing where you wont be alone unless you both want to.
Then you can discuss with her wether she wants a relationship or not if she doesnt want a relationship all the better for you but if she does explain that you dont and stop your advances on her.
Dont be nervous about this it's like bungie jumping you just have to jump or your going to psyche yourself out.
Atleast if you find out how she feels you wont be sitting around putting ice packs on your blue balls. j/k.
Maxmell, I had a nearly identical situation with a coworker many years ago. I was 24 (though not a virgin) and she was 30, a single mom, living with someone out of convenience. We flirted around a little bit for months and she finally said she wanted to set me up with her cousin. We all went to a club one night and did a little dancing. Her cousin was not feeling well so she left and I suggested that this lady and I go back to my apartment and have a drink and watch a movie since she didn't want to go home yet.
We watched a movie and had a bottle of wine in a very comfortable setting. No, touching but there was definitely a sexual tension in the air. At some point, we were looking out the front window and I just pulled her to me. I knew it was the right thing to do, but I can't explain how. You'll just know. She seemed very eager as well.
We were both very up front with each other that this was just a casual,friendly, sexual relationship. Nothing more, nothing less and it never would be anything more than that. The work relationship, age difference and single mom situations just were not something that I felt were conducive to anything beyond a friendship and sex.
Never had a problem and the day after my first date with the woman who is now my wife, I called her and let her know that we had to stop seeing each other. Clean cut, no objections, no hassles with working relationship and friendship.
Now, with all of that said, this was the early 80's when AIDs and HIV were yet to really make the news, but I never failed to use a condom. Further, not everyone can handle this type of an arrangement, despite what they think at the outset. If you choose to pursue it, go slowly and make sure that YOU know what you really want out of the relationship.
Go with your instincts, but be prepared in the event that you're misreading her signals. Good luck.
Hey, age doesn't make a difference. The heart and the personality does.
Think about it, those days with couples dating of the same ages are over. There are many couples out there with young guys dating older women, and younger women dating older guys. It's okay as long as they are in the legal age in your state.
If Ashton Kutcher is banging Demi Moore, then the same can happen to us.
I'm very attracted to older women. I'm 27 years old. I would date an older woman no older than 40 years old. Older women can be sexy and beautiful and very experienced in bed.