[Laurenin]

I've been babysitting for a single father for two years now, since I was 18. His wife died from eclampsia three years ago during labor. We've become friends and know what's going on in each other's lives. He asks me about school - I'm pre-med. I ask him about his work - he's a clinical researcher. We talk about movies, current events, etc. The three of us will infrequently go to a restaurant together if he comes home early and I don't need to rush back to campus to do something.

About a year ago he started dating, which I didn't think twice about at the time. I was happy for him. He's a genuine, generous guy, who's great with his daughter and he deserves to be happy. I do remember the first time he brought a date home. They'd been out a few times before. They came in a little drunk and she went straight upstairs. Apparently tonight was "the night". He asked if I could stay another hour and I said "of course". I didn't mind. I live in the dorms where its unusual if you don't hear moans and groans coming from someones door. And I'm not exactly celibate myself.

I went over to babysit the following Monday and he was a little embarrassed and really apologetic. He said he never would have asked me to stay if he hadn't been drunk and he hoped he hadn't made me feel uncomfortable. I hadn't felt uncomfortable, so I told him I was fine with it and was happy for him that he was dating. So a precedent was set. He would occasionally bring dates home and I would stay for an hour or two while they had sex. Sometimes we would discuss the women he dated and he would ask me for advice about fun dates to go on or for a woman's perspective on various things.

Five months ago he brought home a woman who looked like she was only a couple of years older than I am. I'm pretty sure it was a one night stand, as he had told me he was going out with some friends after work. I never saw her again and he never brought her up in conversation afterward. I had never thought about him sexually before that night. I'm 20 and he's 36 and I've never dated anyone more than two or three years older. I wasn't jealous and chocked it up to not getting any myself for a few months. I went home and masturbated and made it a point to hookup with my FWB a few times to get it out of my system.

Well everything was fine until about three weeks ago. He came home with a girl who is a year ahead of me in our program. We're not friends, but she and I know each other. He didn't know that, but it was awkward. I realized that night I really, really wanted to sleep with him. They dated for a couple of weeks and one night I crept upstairs and listened outside the door while they made it. I actually stood there with my hand in my pants and masturbated listening to them. I feel like such a PERVERT!

I don't know what to do. I'm afraid I'm going to jump him one day. I've fantasized about presenting myself naked, spread wide on his kitchen island for him to come home to after work. I don't want to marry him, but I do want to sleep with him, AND I want to keep being his babysitter and friend. When I think about it rationally I can't see how it could work, but the fantasy is delicious and sometimes overwhelming.

Advice? Thoughts? Some of my girlfriends say go for it. Live out the naughty babysitter fantasy. Some say I need to walk away.

[WildChild]

If you care about the child, don't do it. If you do it will completely change the interaction between you and once it ends it will probably be very uncomfortable for both of you for you to continue working for him. It sounds like he is running through a string of women, do you really want to be just one more?

[Laurenin]

I do care about his daughter. I've watched her reach so many milestones and really enjoy being part of her life. That being said, the current situation will eventually end no matter what. I may leave for med school or if I stay here for school I'll be too busy to babysit. But that's beside the point.

You seem to apply a negative connotation to his dating habits. These aren't weak, wallflower women he's dated. They haven't been run through. Do I want to be just one more? I want to be one. I don't feel relationships necessarily have to have a goal or be heading towards something. I find value in each moment in my relationships. And I'm at a point in my life where I'm really beginning to enjoy sex!

If I did proposition him and we had sex I'm not sure how I would feel the next time he brought a date home and I wouldn't want him to feel he couldn't bring someone home because I was babysitting.

[CHANDLERS WISH]

I think you have to view the word "fantasy".

If it has become a fantasy, can you act it out once, and once only, to full-fill that fantasy, and discussing as you can with him openly that, this is what has occured.

Certainly, I believe that you would be jealous, we are emotional creatures, if and when he bought the next date home...

He actually sounds like a caring man, the fact that he interacts with you and has never propositioned you, the fact that he apologises when he feels he may have made you feel un-comfortable and the fact his wife died, and he is raising a little girl on his own with the help of a babysitter, he's probably not ready for a commitment yet and it's up to the ladies, to decide if they are prepared for just a romp in the hay, in addition you stated some were there for a few dates not one and that he asked of fun places to take them. Maybe he just hasn't found a "replacement" for his wife and I hope he isn't trying to compare

In any event, most nanny's / baby sitters fall for their employer if there is a bit of a bond there in communication...

I wonder if by bringing home younger women, he is actually showing you that age means nothing, who's to say he's not interested in you?

The way I see it, is you have to be straight forward with him and discuss it and see his thoughts on the matter.

Either you two will have a fling one on one, no more FWB on your side, or women on his side, for a while or a one night stand that is with understanding...or agree to leave it in the fantasy world.

But, you know yourself, that if feelings get involved, unfortunately that will end that job... Doesn't mean you can't keep in touch with the baby throughout the years, with gifts, and a phone call, I doubt he'd ever not allow you to do that....let alone him not keeping in touch from time to time...

Discuss it.

CW

[rcoreyus]

I don't think it is such a bad idea for you to sleep with him, as long as you both really understand the situation. If you and he are just looking for a fun partner for the night, or week, and will have no regrets and no unhappiness when it ends then fine. You are both adults.

I'm not convinced it needs to change your relationship with his child.

I don't think he will have any problems - he has been dating and sleeping with multiple women. You need to be VERY honest with yourself about whether YOU would be OK with this situation. If you are, then why not have fun?

[BabyGirl]

I would seriously think about this " Fantasy " and the repercussions of acting it out and also think on how strange some of this sounds.

1) He's bringing home women to sleep with and asking you to stay an hour or so more ?

Why doesn't he just go to these " Ladies" homes and call you & ask you to stay longer then planned ?

How many men or women that are single are comfortable having sex in their homes with a babysitter there ? If they have a child they should be able to have sex after the child is asleep Just like any married or living together people do,in my mind you don't get a Babysitter to watch your child while you are at home so you can have sex in your own home .
If You heard them Having Sex, the child could have also. So what is the point in having you there ?

2) Since he was drunk and asked you to stay abit longer. To me that sounds not only irresponsible ( as a parent ) but insensitive to you. As with respect to your studies and sleep needed .. being as you are a pre~med student and a Woman & Friend to him and a " Mother figure to his daughter " it just ranks of Insult to me.

3) Masturbating outside his door while you are Babysitting is "perverted" in its own as you were there to watch the daughter so he could have sex with some Lady. So who exactly was watching the daughter ? It wasn't you if you were at the door listening. And what would have happened if you were caught listening at the door with your hands in your crotch ? Scary thought there & Embarrassing to be sure.

4) He's bringing home women your age and some are one night stands, others may just be a few dates.

If it is bothering you or making you want to " Have him too ". Then I suggest you just straight up sit him down and explain that you want to have sex with him, but you don't want to babysit his Daughter while he's having sex with other women.

And possibly, since he has no problem with enjoying ladies of your age,you two might try a relationship that includes the friendship you have established, includes the trust of the Daughter that has lost her mother, includes that You are integrated in both of their lives by the relationship you all 3 have with each other

Then if he says that he doesn't look at you that way , simply ask him not to ask you to Stay extra when he needs sex. But if he says Yes, ask him to get a Babysitter for the night while you two go somewhere PRIVATE.

[stressed]

I'm under the impression that you want to have sex with him simply because he has sex with young women your age. Like a feeling of "why them and not me?". Up until he slept with that young woman you had no such thoughts about him = it's not really him you want to have sex with, it's more out of being competitive about it, if not a little jealous as well, as a woman and not because you have feelings for him or you're attracted to him.

This is not a valid reason for you to want to have sex with a man who trusts you to look after his daughter. He obviously has casual sex with a number of women (it does not matter what kind/the personalities of those women, it's what 'he' does) and turns to you as a friend.

You don't talk as much about him as about the women he sleeps with, which enhances my view of you wanting "to show him you're also as good as they are" than you actually want him for who he is.

Don't do it, you'll regret it.

[stressed]

I'd also like to advise you to stop working for him, as this can get out of hand for everyone.

[WildChild]

Stressed has said it better than I did. It isn't a matter of this changing the relationship between you and his daughter but between you and your employer. Why isn't he going to their places? Why come home and have sex with you there?
As a single parent, I too find this a bit odd.

[Teelana]

I agree with Stressed and Babygirl. This situation sounds semi creepy and not at all "right." I think what bothers me most is the that he's been coming home drunk, that he's clearly with a one night stand and/or date is another factor. It's not my intent or place to judge him but if I were baby-sitting someone's child and he came home drunk (more than once at that) I'm not sure I'd be willing to baby-sit again. What he does in his free time is his right and business as long as it doesn't hurt anyone, but in this case it's borderline putting his daughter at risk and you, in an awkward situation. I'd also be concerned that one night he comes home drunk solo and choses to make a pass at you then. My two cents is to get out before something regrettable does happen. Judt do your best to let the daughter know, your chosing to no longer baby-sit is not about her. Don't lose her in all this. Good luck!