A
female
age
26-29,
anonymous
writes:Hello,I'm going to make this question as quick as possible haha!About 8 months ago, I got involved with my boss. He has just quit the company the day we slept together, so technically he wasn't my boss anymore that night, but you get the picture. Anyway, he went to another company and I got a new job myself. At first, we didn't see or speak to each other for 3 months after we had sex, but we started speaking again, and we picked up right where we left off that night. We don't do it everyday, but we'll send sexy text here and then meet up every now and then if we're able to.So, here's the problem. Aside from him, I'm friends with a few people at his new place because they used to work with both of us at our former job. One guy in particular I'm really good friends with and I would go visit from time to time talk and catch up. Before anyone says anything, I would try to go on the days my ex boss was not there, or was already gone for the day, because I may be that girl, but I'm not an obsessive stalker, I know my limits... Anyway, whenever I would go up there, my old co-workers and the other people there would try to persuade me to work there. And then, my ex boss asked me to also, and I finally did.That was short lived, because I realized working with the guy I'm having sex with is not a great idea, and I got a good offer to do something else, so I took it. Well, while I was there I became friends with my former co-worker's younger brother (he worked there also) and we started hanging out. I wasn't sure how he felt towards me, but he seemed a bit immature, and I quickly recognized I see him as a friend only. And I actually thought he felt the same way also..Well, its been almost 2 months since I left there, and I haven't seen the guy in a while, and we only hung out twice in all.. But lately Its been starting to seem like he may like me as more than a friend. He asked me if I wanted to go see a show next week and then today he asked me if I wanted to go to a football game and he said he could wait to see me. Of course, I'm totally down for it! But I dont know if he sees these as dates or if I'm reading too much into it or not.. I mean, I've been having sex with his boss, and my ex-boss, and even though we haven't hooked up lately, we still talk and sext each other. It would be a bad idea if this guy likes me and I give him the wrong impression that I like him too by agreeing to hang out. And it would be terrible if he went back to work and said he took me out the day before and his boss heard it.. So, am I over-thinking this? Are these dates? Or should I avoid hanging with him?
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Fancy yourself as an agony aunt? Add your answer to this question! A
female
reader, Andie's Thoughts  +, writes (21 November 2017):
 It's great that you're being responsible with protection - it's surprising how many don't.
However, whilst I completely understand that you don't want to know, it's important that you do - so you know how at risk you are of diseases (condoms don't prevent them all, as I'm sure you know). Also, if you can't trust him to tell you the truth about who else he's sleeping with, then you really shouldn't be involved with him, as it shows a lack of respect for your health (both from him and you).
A
reader, anonymous, writes (21 November 2017): This is verified as being by the original poster of the questionYes I get all that. We've always used condoms and birth control..He's asked me in the past if I was involved with anyone else and I told him I wasn't, but I've never asked him just cause.. Im not sure, I guess I just rather not know. In my mind, he's not based of things he has said but I'll never really know unless I ask, and even then who knows if its true.Another reason I used condoms and Birth control and just have fun with it because thats what I want anyway.Thanks for all the advice!
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A
female
reader, Andie's Thoughts +, writes (21 November 2017):
I think that, if you want to continue this arrangement, you do need to verbalise it and assess where you are. Make sure it's exclusive or you're at risk of STDs. Also make sure you use condoms every time *and* birth control - no excuses.
If you're mature enough to handle this situation, you need to be mature enough to communicate about what you both expect from this and to do it regularly, so you stay on the same page.
As for working with him, I'm glad you had the sense to leave, as what he was doing was unprofessional at best and sexual harassment at worst, even if it felt kind of nice.
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A
reader, anonymous, writes (20 November 2017): This is verified as being by the original poster of the questionAnd yes.. It seemed like a good idea to work with ex-boss/lover/FWB at first because we worked so well together in the past.. But, as much as I like to have sex with him, his flattering comments about me around my new co-workers made me uncomfortable, and him coming in my office to tell me how badly he wanted to have sex with me and then pretend like we were discussing work when others walked in was fun and all.. But I realized quickly It wasn't the best idea for me. Luckily, I got a great offer to do something else and took that. I would of been wrecked had I stayed.. I can admit that was bad judgement on my part haha.
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A
reader, anonymous, writes (20 November 2017): This is verified as being by the original poster of the questionSorry for responding late! I actually completely forgot I asked for advice haha... And speaking of, it is all great advice.So the thing is, me and ex-boss/FWB dont have a spoken "arrangement" per-say. Its just kind of flowed naturally, and the attraction started the day we met. But as I said, nothing happened until the day he quit his job, and thats when he told me how he felt, and then I confessed also, and you know the rest..It is just sex with us, and thats exactly how I expected it to be, and its worked out fine. So far, none of those "I'm starting to develop feelings" things has happened on my end and I like the "arrangement" just how it is. I will say however, he has expressed interesting feelings towards me before but I've always shrugged it off. Aside from the sex, we have a decent "friendship". We actually talk to each other like normal people would, but I don't talk to him about other guys (even though there hasn't been yet) and he doesn't talk to me about other girls (Probably has been others but I dont know) and I like it that way, I dont want to know.With that being said, this guy that works for him, I ONLY see him as a friend. Even if ex boss wasn't his boss or in the picture, im not attracted to him.. The boy is just too immature for me to ever like in that way. I cant have a serious conversation with him (another benefit I get from the ex-boss/FWB) But as I said, I'm down to be friends, he's very nice. He even invited me to join him for Thanksgiving dinner (and since his older brother used to be my finance manager at my old job with my ex-boss AND works at their new place with them now also.. He'll be there too) and it leads me to believe even more he may like me.. I surely wouldnt want a love tri-angle or any confusion, SO I will just make it clear to him that I see him as a friend if I continue to get that vibe from him.As for serious dating, if I met a guy that I really liked and wanted to pursue a relationship with, I would drop the ex-boss/FWB. As I said, we are able to talk with each other and I'm confident we would still be fine afterwards without any hard feelings.
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A
male
reader, anonymous, writes (20 November 2017): Miss OP saw the potential problems that could result from having sex with her boss and that’s why she found a new job. I think the same potential problems exist for someone who gets close to someone who already is cozy with the boss.
I think that the Aunts who have chimed-in so far have failed to see that OP is talking about a potential love triangle, that is, the OP’s ex-boss lover is the boss of her potential New Guy. So if New Guy and OP start a relationship, New Guy’s boss could become very unhappy and make life miserable for New Guy.
Miss OP should tread very, very carefully and not put Mr. New Guy in a difficult position.
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A
female
reader, Andie's Thoughts +, writes (17 November 2017):
As an addition to my response, your ex-boss only wants sex, so he either wouldn't care that the friend took you out or he'd only "care" because he's possessive, not because he likes you.
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A
female
reader, aunt honesty  +, writes (17 November 2017):
 If you are not interested in the new guy then just let him down gently. If you are wanting to start dating then you should stop having sex with the boss. I mean I don't think it would matter if you went on a date and the boss found out anyway because it is clear that all he wants is sex from you so if you are happy with this arrangement great, if not then look for someone who can offer you more.
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A
male
reader, Denizen +, writes (17 November 2017):
 If you aren't really bothered about the new guy then don't go out with hi if you are worried about future upset. That seems straightforward enough to me.
You say: "It would be a bad idea if this guy likes me and I give him the wrong impression that I like him too by agreeing to hang out."
And you also say: "It would be terrible if he went back to work and said he took me out the day before and his boss heard it...."
Why would it? You are a free agent. So in answer to your question, yes, I believe you are over-thinking and overcomplicating this.
If it looks like the new guy is getting serious then you need to put him straight. It is only fair.
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A
female
reader, anonymous, writes (17 November 2017): Not sure what it is you're looking for.
A steady boyfriend or somebody to have sex with?
Clearly the ex boss is just a hook up. Nothing more.
And what about this friend? Would he be another hook up?
Not sure you know what you want?
But if it's a boyfriend, dump the ex boss and take it slow with this other guy. Unless you're into bed hopping.
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A
female
reader, Andie's Thoughts +, writes (17 November 2017):
OP, listen, when you start *thinking* about dating, the FwBs have to stop.
Think about it, it comes out that you've been hooking up with someone literally days before or during dating someone - logical or not (because of unspoken exclusivity), it's not something that will be seen positively or neutrally. You may very well ruin your chances with someone you actually like because you're hooking up with someone else around the time you start dating them.
You need to learn to communicate. You want a FwB? Communicate. You want to know if someone is interested? Communicate. You want to hang out without leading someone on? COMMUNICATE. You're an adult and doing adult things, but not communicating like one.
You need to call him a friend or something to let him know where you stand. Besides, you may actually develop feelings for him or someone else, once you detangle yourself from the former boss.
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