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Should I ask him if he's ever had sex with her?

Tagged as: Friends with Benefits, Sex, Three is a crowd<< Previous question   Next question >>
Question - (18 January 2018) 16 Answers - (Newest, 26 January 2018)
A female United States age 26-29, anonymous writes:

Hi guys! Quick question..

I've been having a sexual relationship with a man for almost a year. We used to work together but we now both moved on to other jobs right after the first time we had sex.

So here's the thing- Right before we had sex the first time, we were talking about people at work that we thought were good looking. I asked him about a girl that worked there, because she's very pretty and I was always curious if he ever hooked up with her, but I didnt want to flat out ask, so I asked him if he thought she was attractive.. But when I asked him, his response was "She's pretty for a black girl".

Immediately he felt bad for how he said it.. And he corrected himself and said "I didnt mean it like that, Im just not really attracted to girls like her". Basically, he thought she was was pretty, but didn't find any sexual interest in her. And I understand, everyone has their own preference and some people are only attracted to certain races, and not other races, no big deal.

I never thought about it again, until recently. I was helping him with something on his phone, and a text from her came up, but nothing bad. I gave him his phone and I told him she had texted him. He started talking to me about how she was pregnant and he was asking her she was showing already or not. I already knew she was pregnant, and I just said "Yeah- you can definitely tell she is! I'm happy for her!"

We met up later that night and right before we had sex, we were talking and I made a somewhat assumption that he has alot of girls like me. I didnt say it in a bad way or an accusing way, but he almost took offense to it. He said that wasnt true and was very surprised I would assume that about him. I mean how could I not? But I felt a little better after that and just let it go.

But now, again, im wondering if he ever slept with that girl. He can be with whoever he wants, but if its someone I know or is a friend, I couldn't continue anything with him. We can be friends, but It just wouldnt feel right in my mind, even if it happened a long time ago. So im wondering, is it worth asking, or would I be invading his business?

View related questions: at work, text

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A reader, anonymous, writes (26 January 2018):

This is verified as being by the original poster of the question

I was very surprised by his comment about her being pretty for a black girl, but I could tell he didnt mean for it to come out that way. He know i'm half black, and apparently he likes bi-racial women. I guess he meant to say he is not physically attracted to 100% black women.

But regardless, before I was involved with him, I had a boyfriend I was with for 4 years and we just grew apart. And then I got in a intimate relationship with this guy. Since we started having sex, I've only met ONE guy that seemed to fit everything I wanted. He was around my age, single, handsome and was so kind and down to earth. I felt so blessed that I met him. And as soon as I did meet him, I completely forgot about this other guy. I didnt talk to him at all and I didnt miss him even a little.. Because I wanted to actually date this other boy, and I felt like I finally met someone who was relationship worthy.

Unfortunately, I hung out with this boy late at night one day, and I realized he only wanted sex from me. Now, If I only wanted sex then I would of went for it. But I saw more in him, so I didnt have sex with him. That was the last time I ever saw or heard from him. He never spoke to me again.

I was honestly very broken over it, I cried for days (hate to admit that) but I haven't been excited over a guy since I was probably a teenager. My ex and I broke up a year ago, and it took a year to meet someone I truly liked, and I felt like I was dating for the first time and I was getting hurt again for the first time.

Every other guy that I've met, I was not 100% into, but I gave them all a chance, and EVERY one was looking for a FWB. One guy even texted me not to long ago just to check and see if I'm still a prude. And one other guy was decent enough, but every date he set with me, he cancelled. Like at least 7 in a roll. Then I never heard from him again.

The point is- Its not that im not trying. I am trying. My mind and my heart is not closed off to a real relationship, I would love a real relationship- I just keep falling short. I can't experience a relationship until I find the right person.

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A reader, anonymous, writes (24 January 2018):

Sweetheart, you're taking the advice all wrong. Nobody's condemning you for being female and enjoying casual-sex with a guy. It's about your age and your attitude towards sex and relationships. You have so much to learn and experience.

You need to develop and practice how to find and maintain meaningful and healthy relationships.

Could it be the others have failed; because you need more experience in these areas?

Maybe the other guys see your immaturity and difficulty in handling a relationship?

You can blame them or say they weren't offering what you're looking for. It could also be the other way around.

By the same token, we can argue that's attributed to your subconscious-fear of letting go of your FWB-partner; who might find somebody else to take your place. Visualizing him with a certain person would touch a nerve.

It shouldn't at all!

There's always an irritating hidden-truth about certain things people refuse to accept; because they're trying to bury or suppress it. They're in denial.

The mere fact you miss the point altogether, is due to your limited understanding and youth.

Men and women think differently about sex, and we express our emotions very differently. He's enjoying sex with you and any other women as he pleases; with no concern about who or what you're doing. Yet you would feel "weird" if he had sex with a friend. One female in particular. That's a territorial-instinct. FWB set no boundaries and have no concerns of that nature.

As a side-note. I think you feel as uncomfortable as I did about his comment about the co-worker's looks considering her race. I'm biracial too; and very irritated by the ignorance of people and their seeming inherent racial bigotry. You've kept it secret from him. Why?

The problem with casual or recreational-sex is its desensitizing properties. Real-sex becomes detached and no more emotional than masturbation. People are just someone to use, and you're done with them.

The more frequent you practice it, the less you're able to attach your feelings and emotion to it. For anyone! It no longer is a an expression of affection; but just something you do to get-off.

If he is sexing other women; his frequent activity also raises the risk of STD's. HIV and herpes being the two worst and topping the list. There are now strains of gonorrhea and syphilis that don't respond to antibiotics.

You're so very young and have so much ahead of you. All you need is an unplanned-pregnancy or a life-changing infection.

So you can brush-off advice coming from a good place for everyone of us who cares; but some people learn things the hard way. I just like to plant a seed of wisdom; and it sits there in the back of your mind. Maybe it will slowly grow as your better judgement and understanding develops. Then sometime on in the future comes the epiphany, or that AHA! moment. "So this is what they were all talking about!"

I never waste my time upset about those who don't need my advice, or rebuff it. Too many people read these posts who can benefit from the advice, to hurt my feelings about that!

In any case, I care and wish you well!

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A reader, anonymous, writes (24 January 2018):

This is verified as being by the original poster of the question

What I've tried to explain is that we like to have sex with each other, and we both use each other in that way. If were both on the same page about what we're doing- I dont see how he's "using me". He's not using me anymore than I'm using him, but I know society has this outlook on women that they cannot possibly do the same things men do when it comes to sex for some reason, but I'll leave that up to you guys to figure out..

As I said, I've tried dating other guys and nothing has worked out so far. If I met a great guy, I wouldn't continue having sex with this other guy. He's fun in the meantime. All I said was if he did have sex with a friend of mine, it would be weird for me. And I wondered if I should ask. And no, I didnt say we are GREAT FRIENDS. I was never going to say that.. I didnt expect to be jumped on just for being curious. He's tried asking me about weather or not I've had sex with anyone else, but since I was curious about someone specific, I wasn't sure if it was appropriate. Thanks anyways though..

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A female reader, 02DuszJ United Kingdom +, writes (20 January 2018):

02DuszJ agony auntWhy don't you go and live in the bunny mansion if you're happy to be used as one of many women? Come on you're worth more than this, cut it off and get out there and develop yourself as a person- find a passion and work towards achieving a goal- live the single life and find your self worth. You don't realise it but this guy has more USE for you than you have for him! And you will have much more fulfilling relationships if you work to improve your self and your life..

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A reader, anonymous, writes (19 January 2018):

This is verified as being by the original poster of the question

It is mostly just a sex thing.. I mean Im trying to date single guys my own age, but I continue to hit dead ends. He is convenient for sexual reasons, but if I met a guy worth my time, I would drop him for sure.

Recently, I actually did meet a guy that I thought was great and I was pretty excited about it but in the end he wasn't the one for me. So I continue to be single, and hopefully I'll meet someone nice one day.

But as I said, the guy is great for sex- which is exactly what I was wanting with him, and thats what he was wanting with me. Of course, me being a woman, I have more feelings about stuff, but I dont get it confused. I dont get caught up.

I was surprised that he said he wasn't into her, since I myself am half black (I guess its hard to tell), but I believed him when he said it so I guess I shouldnt question it.

Thank you all for the advice!

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A female reader, Honeypie United States + , writes (19 January 2018):

Honeypie agony auntOP, so you are OK with this casual sex going on (him sleeping with MULTIPLE women) but he can't have slept with someone you know?

And if she is your friend, don't you think SHE would have hinted at it or mentioned it?

I think you are WAY more invested in this guy than he is with you. You are just ONE of TWO (or more) women who satisfy his sexual needs. I really don't get you young women wasting your time, emotions, affection, bodies, attention of guys like this.

Your life, your choice.

Still, why waste your time on a guy who think you are only good as a penis holder, not much else?

(and please don't say you are GREAT friends.... because that is not how GREAT friends treat each other)

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A reader, anonymous, writes (19 January 2018):

Might be time to ditch this relationship and find something more meaningful for yourself.

You are feeling jealousy and discomfort about his other sexual-partners. You won't admit it, but your feelings are changing towards him. You're not getting the kind of emotional feedback someone your age deserves. You should be practicing on how to conduct a real full-fledged relationship with meaning and all the fixings. In the back of your mind, you are craving a monogamous relationship with this guy.

That one particular pretty girl triggers your insecurity and raises your suspicion; because she is the one girl whom you feel you can't compete. The reason? Because she's exotic and "different."

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A reader, anonymous, writes (19 January 2018):

This is verified as being by the original poster of the question

I already know about one other person he is sleeping with, it doesn't bother me- I was only concerned if it was a friend of mine.

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A reader, anonymous, writes (19 January 2018):

This is verified as being by the original poster of the question

It doesn't matter how many people he's been with, and your all right, its not my business who he has been with. It only bugged me because I'm friends with the girl. If its a stranger, some other girl that he met somewhere else, that means nothing to me, as long as he's being safe. But a girl that I hang out with, it weird for me. I wouldnt be mad or anything if that was true, I just wouldnt feel comfortable having sex with a guy who is sleeping with me and my friend. I mean, he's told me before If I slept with a friend of his, it'd make him feel weird- So i'm sure he'd understand.

And the thought of him being the father never crossed my mind actually.. I mean if one day it was revealed that they did have sex and he was the father, I would be legitimately shocked- and I'd feel awful for her boyfriend.

I was just wondering if I should ask- But I guess I wont. Thank you for the advice!

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A female reader, DancerGirl1984 United Kingdom +, writes (19 January 2018):

His sexual past is non of your business and you have no right to ask him about it. Your sexual past is non of his business either. As long as both of you had a full sexual screening before getting together and it was clear, anything before that is private.

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A male reader, anonymous, writes (19 January 2018):

You have already slept with him so why ask now? I think he has already answered your question that she is not his type. I say let it go.

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A male reader, N91 United Kingdom +, writes (18 January 2018):

N91 agony auntI really don't think it's any of your business.

You were work colleagues by the sound of things not best friends, so even if he had slept with her, even though I really doubt he has from your post, why would it matter? What will it change whether he has or hasn't? You suddenly don't like him anymore because he's slept with someone you know?

I think if you're in a FWB situation with this guy and this is a main priority for you, then you're already in too deep. If you're considering stopping a strictly sexual relationship because of who this guy may or may not of slept with in the past suggests to me that you have deeper feelings for this guy.

I think something you actually DO need to ask, is 'where is this situation headed?' Are you happy being used as a place to hold a penis for a short while? Or do you value yourself higher than that?

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A female reader, 02DuszJ United Kingdom +, writes (18 January 2018):

02DuszJ agony auntWhy are you *just* in a sexual relationship with him? You obviously want more for YOURSELF so why settle? If in fact this is just friends with benefits then surely you logically know you're not exclusive! In other words he can have as many slices of whichever pie he wants, you have no claim over him.

I think NSA FWB sex is demeaning- men are literal and they take your word that you're ok with it.. they don't get attached in the same way women do because they're emotionally wired differently. So where does that leave you? It leaves you with feelings of attachment where as he sees you as pretty much a blow up doll.. in the harshest terms that what FWB is

Don't you want to meet someone and click with them, because you BOTH love each other's company, doing the same thing, fun things getting to know each other, and strengthening that bond? Not having to worry about if he's into you because honestly? When a guy WANTS a relationship with you it's clear as day! If after a year he's not wanting more he's not from you he's a WASTE OF TIME.. and I think obsessing over how many other partners he has is the least of your worries with this one.

Because really? On paper he's officially allowed to see whoever he wants.. you're just there for bedtime.

Want more for yourself- more than he wants for you, you are worth more

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A female reader, Youcannotbeserious United Kingdom + , writes (18 January 2018):

Youcannotbeserious agony auntSo are you saying that anyone who has dated anyone you know it automatically out of bounds? Wow! Glad not everyone thinks that way. I have been in a relationship for many years with a man who I met when he dated one of my closest friends. After they broke up, we got together and even attended my friend's wedding with her new partner. It was all very civil. I never felt I had crossed any lines and my friend never felt I should not be dating someone she had previously dated.

Unless you suspect he is the father of the baby (you don't say this but perhaps that is your worry?), it is really none of your business whether they dated/had sex or not, especially as it will be a deal breaker for you. Let it go. IF it happened at all, it was before you two were an item. Stop tormenting yourself about it.

If you DO suspect he may be the father of the child (not sure why you would but maybe there is stuff you haven't told us), then you probably DO need to ask the question as, if you stay close, this will affect you as well.

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A female reader, Honeypie United States + , writes (18 January 2018):

Honeypie agony auntWhy is it any of your business if he slept with her or not?

Unless the BABY she is carrying is his, who the F cares?

No, you don't ask, you are not OWED a list of his previous partners. Just like it's NONE of his business whom you have slept with before.

Bringing up old lovers, hook-ups, GF/BF's and sex partner is NOT going to make a relationship better. It only creates drama.

Why do you feel it is any of your business? Why do you need to know?

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A reader, anonymous, writes (18 January 2018):

Friends with benefits usually don't concern themselves with past partners, only that their partner is disease-free.

You wouldn't be so concerned unless your feelings are more than just friends.

Why open a can of worms? It's none of your business if he had sex with her in the past. What are you insinuating? Maybe he might be the father? Now that might be a good question to ask. It would mean he has some responsibility for the child.

If you're concerned about their connection; then you are crossing into territory beyond just being FWB. If it was just sexual, what he does with other women wouldn't matter.

The whole issue behind this is that you're catching feelings; and becoming very emotionally-attached. Feeling jealousy is proof. If he's not on the same page, you're going to end-up with hurt feelings.

"She's pretty for a black girl". That makes my skin crawl.

I am so exhausted with the insensitivity and the race-conscious climate in the USA! Technology is evolving while people devolve. Youngsters should have gone further in their thinking than the oldsters!

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