Awkward situation (As much advice as possible please)

So to make a long story so much shorter, theres this chick at work, I spend all my time with her and we get on like a house on fire, have done for about a year. Something happened yesterday that I didn't expect, we kissed. We were all over each other for the rest of the day trying to avoid getting caught by anyone at work (which more then adds to the thrill!) shes good looking, slim with a great body and is everything I could as for. However heres the kicker..... shes nearly 40, I am 23! Now obviously this can't work (and if you think it can, well truth betold I would rather be with someone of similar age) but now 24 hours later, shes crazy about me and can never wait to see me.

Now I am in the situation where I feel trapped, I mean I like this, I love this, I enjoy being able to kiss her and hold her and get close to her but I know that long term this can't work! But I dunno what to do... any advice would be appreciated : )

P.S I am not doing myself any favours by replying to her lust-struck messages with a similar tone. In other words? Leading her on.

Perhaps she's not looking for anything long-term, I'd say make that clear. After that, well, who knows

Report her to your boss, get her kicked the fuck out. Now you have an open spot for a friend! Or a better office for yourself! All problems solved!

Report her to your boss, get her kicked the fuck out. Now you have an open spot for a friend! Or a better office for yourself! All problems solved!

Umm, man up and **** the **** out of her? Just 'cause she's hot for you doesn't mean she wants to marry you - worry about that if/when it happens. Just don't do anything stupid.

I don't know, but I'm kind of imagining ew. Then again, maybe I'm imagining incorrectly. How old is she exactly?

TALK TO HER! Before it gets any worse, just talk to her and lay things out. You could get through this in the best possible way, by having a particularly beneficial friend, if you know what I mean, while not being attached and allowing for exploration with other people. But dude, talk to her first. Can't stress that enough. No point in messing around with her if it's going to go pear-shaped eventually. Figure the ground rules out, and then you can dive deep.

As is customary:

@NTM: 39

@RPGee said:

TALK TO HER! Before it gets any worse, just talk to her and lay things out. You could get through this in the best possible way, by having a particularly beneficial friend, if you know what I mean, while not being attached and allowing for exploration with other people. But dude, talk to her first. Can't stress that enough. No point in messing around with her if it's going to go pear-shaped eventually. Figure the ground rules out, and then you can dive deep.

As is customary:

Argh... now I gotta somehow find the balls to initiate the conversation : /

What are her messages like? More say... Cock hungry or wants a relationshipy.

@konig_kei said:

What are her messages like? More say... Cock hungry or wants a relationshipy.

Soppy can't stop thinking about ya messages.

does she have any kids? if she does, you should bail immediately before you lead her on too much.

otherwise, i say it's fair game as long as you send some clear vibes that you're not interested in a long term relationship.

@Silock said:

@RPGee said:

TALK TO HER! Before it gets any worse, just talk to her and lay things out. You could get through this in the best possible way, by having a particularly beneficial friend, if you know what I mean, while not being attached and allowing for exploration with other people. But dude, talk to her first. Can't stress that enough. No point in messing around with her if it's going to go pear-shaped eventually. Figure the ground rules out, and then you can dive deep.

As is customary:

Argh... now I gotta somehow find the balls to initiate the conversation : /

Fuck yeah you do! Be a man, and show her how much of a man you are! Unless you're actually Katy Perry, in which case show her how much of a Katy Perry you are.

Seriously, though, it'll help. It'll set up your confidence for when you really need to ask someone out, it'll make sure shit doesn't go wrong (unless she's, frankly, insane and manipulative) and you retain the ability to have this option for you.

Just so you understand: you, according to this, have the option of free, unattached, and potentially wildly satisfying sex here. Take it where you can, sir, it does not come often.

This sounds extremely awkward. Talk to her before you feel worse, dude. TIS THE ONLY WAY.

@drGiggless: She has an 8 year old son! Going pictures with her and him later on : / Won't be doing anything though, don't want her son knowing theres something going on.

I don't understand. You're enjoying what you're doing, yet you believe it isn't going to work for you. Dude, it's working for you if you enjoy it. You don't actually care about age you just seem to want a relationship in your age range to fit the social norm. Who cares if she's older? You're enjoying yourself and she is too according to you.

Just keep doing what you're doing, I say.

@Silock said:

@drGiggless: She has an 8 year old son! Going pictures with her and him later on : / Won't be doing anything though, don't want her son knowing theres something going on.

Well I was leaning towards thinking that she just wants some unattached sex with a 20-something year old guy.

Now I say get out immediately. A near 40-year old single mom doesn't have time for friends with benefits with someone who is 16 years younger. She probably actually likes you and thinks a relationship can work.

I was gonna say continue until you mentioned she has an 8 year old son. I'd say it's fine as long as she's OK with keeping it purely sexual and the son doesn't find out. But the "miss you, can't wait to see you" messages could indicate that she wants something more. Keep it going until she gets fed up and either tells you straight up that she wants more or leaves.

I hear what you guys are saying, but this is gonna be so tough to do. Its gonna kill her.. I fucking hate upsetting people!

Okay, now that I know she has an 8 year old son that kinda complicates things. At first this just seemed like harmless fooling around but now eeeeeeeeee be careful with that.

This is why you shouldn't get involved with people at work. Holy shit is that going to be awkard.

I don't blame you if you don't have the guts to tell her off. You could always stick it out for awhile until you find a new job and then vanish into the wind. Lol.

@drGiggless: She has an 8 year old son! Going pictures with her and him later on : / Won't be doing anything though, don't want her son knowing theres something going on.

@konig_kei said:

@Silock

@drGiggless: She has an 8 year old son! Going pictures with her and him later on : / Won't be doing anything though, don't want her son knowing theres something going on.

Bad idea bro. Going to the movies with her and her son, she wants something more.

Yet, if nothing else shes still a great friend and I would be going cinema with her if this wasn't going on..

Alright, I'll be the first to admit that with a child involved, that exponentially complicates things. Hmm, this is not as easy as once thought.

Still, my advice is: Talk to her. Ask her her thoughts, talk about yours, that sort of thing. Funny that a little talk can help, I've always found.

@konig_kei said:

@Silock

@drGiggless: She has an 8 year old son! Going pictures with her and him later on : / Won't be doing anything though, don't want her son knowing theres something going on.

Bad idea bro. Going to the movies with her and her son, she wants something more.

This definitely. If it was just physical, she would hire a babysitter. She's testing to see how you get along with her son.

@RPGee said:

Still, my advice is: Talk to her. Ask her her thoughts, talk about yours, that sort of thing. Funny that a little talk can help, I've always found.

This is the best advice. It's the only solution that can end with a good outcome.

You guys are right, I just gotta talk to her about this.... shit, I'm gonna hate this.

@Silock: You're 23! Fucking ENJOY LIFE! GET IT! You don't have to pursue a relationship to have fun! I highly doubt SHE wants a relationship. Keep it out of the office, and have fun! All you people saying "break it off NOW" are real Debbie Downers.

@Silock: You'll feel much better afterwards, though, believe me. And MUCH better than a time when you'd regret not talking to her.

@OllyOxenFree said:

@Buscemi said:

Report her to your boss, get her kicked the fuck out. Now you have an open spot for a friend! Or a better office for yourself! All problems solved!

Steve Buscemi is wise. Listen to him.

Are you both insane? KEEP ON HITTING DAT ASS MAN!

Dude, consider that she might not be totally oblivious to the fact that there's a 17 year age difference between you. Chances are that she's not looking for a serious relationship with a 23 year old.

There is, however, a very real chance that she's looking to bang you. Repeatably. And for that, my friend, you should thank your lucky fucking stars.

@InsidiousTuna said:

@Silock: You're 23! Fucking ENJOY LIFE! GET IT! You don't have to pursue a relationship to have fun! I highly doubt SHE wants a relationship. Keep it out of the office, and have fun! All you people saying "break it off NOW" are real Debbie Downers.

I'm hearing ya, but once a kid gets involved its no longer 'just for fun''. She has a life, she clearly must be looking for a partner.

I would have guessed she was just after a fuck, but the son intro this soon? That's a really bad sign. You need to let her know you aren't after a relationship ASAP. To be honest, you're making her sound ultra needy, so I expect it isn't going to end well for you or her. Best case though is that we are all wrong and she does just want to screw. If that's the case she's probably going to blow your mind

why not enjoy it for what it is: a nice fling that spices up the workplace.

not everything has to end up in a hardcore relationship which inevitably has to lead to marriage and whatnot.

Both sides of the arguements have good points.

You have the break it up crowed who are right because it could end up upsetting her in the long run and she might not beable to recover so quickly.

The keep up crowed are right because it is just a bit of fun and as long as i'm careful and don't knock this bird up, it is just a bit of fun.

Its tough to decide who to side with, I don't like hurting people but on the same token, I love fucking people.

@DeF: Except it's not a fling at all. They have known each other for a year and now that they finally kissed, he is meeting her son. OP is trying to be a responsible adult about the situation. Normally I would be all for the "sex now, ask questions later" route, but that doesn't seem fitting here.

Hmm, too quick on the draw there. Didn't read the part about the son intro situation. Let her know that you're not in any way looking for a relationship. Straight up. The sooner the better.

@OllyOxenFree said:

@Buscemi said:

Report her to your boss, get her kicked the fuck out. Now you have an open spot for a friend! Or a better office for yourself! All problems solved!

Steve Buscemi is wise. Listen to him.

Are you both insane? KEEP ON HITTING DAT ASS MAN!

I'll do the talk face to face with her at work on Monday.

I don't understand. You're enjoying what you're doing, yet you believe it isn't going to work for you. Dude, it's working for you if you enjoy it. You don't actually care about age you just seem to want a relationship in your age range to fit the social norm. Who cares if she's older? You're enjoying yourself and she is too according to you.

Just keep doing what you're doing, I say.

It helps knowing that when comparing my situation to alot of other peoples suck as the scenario where someone has killed someone and is on the run, or someone who is in the middle of a drug smuggle right now and is at the airport going through security.. my problem is pretty tame in comparison. I just keep thinking this to myself lol helps me feel better!

I was all in for this until you mentioned the kids, get the fuck out of there.

There probably wouldn't have been too much of a problem until the kid showed. She still could just be DTF, but kids usually means something more. I know age is "just a number," but I typically stick to the proper age range to avoid situations like these. I can't imagine being 40 and fucking around with a 23 year old. That sounds like the worst. No offense.

@drGiggless said:

@DeF: Except it's not a fling at all. They have known each other for a year and now that they finally kissed, he is meeting her son. OP is trying to be a responsible adult about the situation. Normally I would be all for the "sex now, ask questions later" route, but that doesn't seem fitting here.

I was going by the original post info only. The kid changes things, obviously.

the responsible adult thing is -> talk about it!

She's not looking for a long term thing either. She probably just wants to have some fun for a bit. Enjoy it. Your summer fling, for you and her, will probably end in 2 months tops. Enjoy.

The first question you have to ask yourself, is would you have a relationship with her if it wasn't for the age difference? Look, just because society's general norms indicate you should date someone extremely close to your age, it's not like it's law. As you start getting older, age means less and less. You're coming out of an awkward stage where you start to realize that. When you're young, you have to go with someone else young. That actually is the law. But, once you start getting later on in your twenties, you realize that it's about the person, about how much you care for them, not just about the number attached to them.

Now, with that said, if you really don't want to continue this relationship, and you feel this isn't going to work, I say talk to her about it ASAP. If it was just you two fooling around, it wouldn't be that big a deal, but now that she's introducing the kid, you're in red alert mode. Stuff's about to get serious real dang quick unless you do something. So in other words, this is your make or break moment. Regardless of what you do, I wish you luck.

Lead her on for a while, then suddenly shut her out of your life...

And hide your rabbit...

So she's a 40 year old single mum who pulled a 23 year old guy, sounds to me more like she's just looking for some male company more than anything else. It's probably pretty tough to be a 40 year old single woman given that most men in that age range are likely already seriously involved with someone. And it must be even harder being 40 and also a single parent. I doubt she gets much time to actually go out and scout for potential partners let alone get into any sort of fling or relationship with men her age.

As some have said she may just be DTF, looking to find someone to keep her bed warm on a Friday night sort of situation. On the other hand she may actually have fallen for you, I mean if you were in her shoes and had a 23 year old woman who you got on with and spent a lot of time with you'd likely find it hard not to want to take it to the next level.

At the end of the day you need to talk to her, find out what she wants and what she's looking for and see if it suits you and your own needs and wants. If you both come to a common ground then go with it, if not then nip it in the bud before it goes too far.

Announce that you are moving to a different country. See if she chases after you at the airport. If she doesn't, then you're good. Otherwise, talk to her.

Serious Answer - TALK TO HER