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I have a feeling that my best friend is dating my younger sister secretly. Unfortunately, he has a reputation of dating multiple girls. What do you suggest I do?
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There is nothing wrong with that not unless you don't want your best friend dating your little sister but, the fact he dated a lot of girls is not good either.

19 Answers

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Best answer
If he is your friend, you should ask him directly if that is the truth. Your instinct will tell you what to do and confront him. I think you are doing this because you love your sister so much and don't let your friend ruin your sister's feelings. Sometimes in love, we are blinded by the bad reputation of the person we love that is why it is difficult for us to listen but still be a big brother to your sister and ask her too. Let her know what is your friend's attitude towards other girls. Let her know the truth. If she don't listen, it is not your fault already. But start with asking your friend first and ask him not to lie to you. Tell your purpose. Tell him that you are not ruining what they had started but you just want to know the truth and save your sister.
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I completely agree with you. It will be best for me to ask my friend if really he is dating my kid sister, and if he admits i should tell him right a way not to hurt my sister. And afterwards, i can also have close discussion with my sister not to dent my friend's image but warn her the dangers that lie ahead in she dating my friend.
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Please let us know what happened? I think you are only doing it because you don't want to ruin both. Both of them should appreciate you.
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You doing great for protecting your sister from this horrid person, I know he is your best friend,but protecting your sister is the best choice.
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I never see  anything wrong with ones best friend dating one's sister or any family member for that matter only if the intentions are pure.Your best friend I'm sure have no blood relationship whatever with your family so there's absolutely nothing wrong with that but what I have problems with is the intentions.

In your case your friend in question has the reputation as a womanizer and a player and this should makes fear kick in, because a lot of people don't value friendship they might do whatever pleases and damn the consequences,after all he will just believe the highest you can do is stop being his friend.you have to search it out and be sure he is actually dating your sister and if it true,monitor the affairs a bit,tell your sister about his reputation with the opposite sex and tell your sister to be very careful or she should outrightly quit the relationship that's if they're actually dating.
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Quite reasonable contribution you gave. But don't you think if my sister has fallen deeply in love with my friend, it might become impossible for her to see my reason for her to quite the relationship?
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This are exactly my thoughts the real intention and motive should be found out before the relationship goes too far if it is really there. Like you have said many people may do it just to prove a point and others may do it just for the fun of it and that"s not good. It may not settle well with others.
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You must talk to your sister about that, if she fall deeply, try to be  there for your sister most of the time and protect her emotions. Sometimes, we can't stop people from loving a person it just happened.
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It's natural for you to want to protect your sister but as long as she is not in any danger I would let her deal with it in her own way. Why are they dating secretly? Is it because they know you wouldn't approve? I know my son used to hate it if his friends were interested in his sister!

They won't thank you for interfering in their lives and she might even settle him down so he will lose interest in other girls. Keep an eye on things and if they do go wrong then be there for her because she will need a shoulder to cry on. I suppose you could always ask her about him so that things are out in the open because I think you would feel better about it if it wasn't a secret and they were being honest with you but try not to be too judgmental because it may turn out well.
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Yeah! You are right, it could turn out to be they were met to be so i don't it should be wise for me to interfere with destiny. And besides, she has her own life to live.
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Some guys feel like it is weird. Even when they are not blood relationship, they feel like it is awkward for two personal people in their lives to be romantically involved. Others feel the need to protect their loved ones because often times, they know what the other person is capable of. The good and bad.

Since you mentioned his reputation with girls, it is nice to have a talk with them separately. Don't be confrontational about it. It is just to know what is going on. You can give your sister advice and be there for here. It isn't wrong so don't make them feel like so. Tell your friend to be honest about his feelings towards you sister and let her make her own decisions.
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You are correct, and I appreciate your take on this matter. There is possibility the guy might because of my sister turn a new leaf of being a womanizer.
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You really have to save your sister even if we if it will cost your friendship. Here,we are talking of blood which is thicker than water. If your best friend was a good person and can stick to one single girl, then I would have no problem with him dating your sister. Dating multiple girls has its side effects and your sister might end up being hurt and am sure you wouldn't love to see her hurt.

Now the problem comes in when you want to terminate the relationship because if they're dating secretly then they probably love each other. Your sister might feel like you're jealous of her and this might bring another issue. Maybe you should sit down with her then explain yourself and she might listen. If she doesn't listen then you should let her be until she realises that out by herself.
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Indeed, i should care for sister enough to the point i wouldn't want to see her get hurt. The key thing here is being diplomatic in dealing with this issue because if not there is tendency of losing both my sister and my best friend.
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First and foremost this is your small sister your supposed to protect her always from any kind of danger. If your best friend has good motives towards her,  why is he dating her secretly he should be comfortable enough to even talk to you about it he shouldn't hide his intention. Especially now that you know he has a reputation of dating many girls. I suggest you talk to him and ask him if he is truly dating your sister don't live in assumptioms. We all know assumptions are npt good and they can be costly at times. Don't take chances save your sister from hurt before she becomes a victim. I think its good to be each others keepers that's one thing i don't take for granted with my siblings so do what you have to do that's my take.
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For sure, it won't be right for me to make assumption of something i am not sure of yet. Perhaps i should dig deep into the matter before drawing conclusion and then deciding what to do next. Thanks bro!
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I personally wouldn't do anything about it. This is me. I think about what it would do to our friendship and how badly I could hurt my younger sister. I would wait until one of them came to me first and told me they were dating before I told them how I feel.

This is not you, and I understand this. If you feel so strongly about your best friend dating your younger sister you can try and have a talk with your sister. Find out if she is actually dating him and if he has a strong feeling towards him or not. You can tell her about how many other women he is dating and to be careful to not get hurt or too involved with him. All you can basically do is to warn her and let her know what type of a guy he is. Tell he why you keep him as a friend and not someone you'd ever date.

You can also talk to him and tell him how you feel about this and how you don't want to see him hurting your sister. Let him know that he is being unfair to her by dating other women at the same time. That is about all you can do if you don't want to hurt either one of them.
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I guess that will be the perfect thing to do in this critical situation. I should tell my sister the dangers involve in dating my friend but if she decides not to listen to me whatever happens to her is her business. Thanks.
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Just be careful to not destroy your relationship with your sister. Just sit down and start talking about your best friend and tell her that you have some concerns about him and how you don't think it is right how many women he dates at the same time. Talk to her as a friend and like you are confiding in her about a secret you know about him. Tell her that you don't want him to find out that you've talked to her. Maybe this way it will be easier and she will get the hint without you telling her that you know she is dating him. 
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I don't think there's something wrong if your best friend is dating your younger sister so long as his intentions are genuine. Perhaps you tend to be so wary about this because as you said, he has a reputation of dating multiple girls. However, I think your sister won't like it if you will stand between them. My advice is that for you to let them be and show them your full support. That way, she will know that she can trust you, and that she can tell anything to you.

As a best friend, I think he also doesn't intend to hurt your sister because he respects both of you. So just believe in them, and have faith that all people can change no matter how complicated their past is.
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Thanks for your answer! But I said they are dating secretly, meaning that non of them has confided in me to tell me about their relationship.
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If you know his CV of dating many girls, it means he's a womaniser , and why would you let your sister get into the hands of such a man with low morals. Talk to your sister woman to woman talk and let her know what she's getting herself into
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depends on how young your sister is? Mostly know but keep in mind if they have a breakup it's a higher chance you may lose your best friend. Even if they tellyou. If course not.
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Definitely, there is nothing wrong with your best friend dating your sister. It is up to your sister not to continue the idea. Don't be worried. She can handle this.
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From what you have stated, I feel it's not right for your bestfriend to date your sister. But because they are already dating I feel you mentioning your best friends wrong ways to your sister may cause conflict between the two of you. At this juncture I feel you should approach your bestfriend and let him know that if he hasn't cut his bad tendencies of dating multiple women there is going to be a problem between the two of you. 
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It's understandable that you would have reservations about your best friend dating your younger sister. It's important to communicate your concerns with your best friend directly and honestly. Make sure to let him know that you care about your sister and want to ensure that she is respected and treated well. You could also speak with your sister and let her know your concerns, so she is aware of the situation. Ultimately, it is up to your sister and your best friend to decide if they want to pursue a relationship.
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There is nothing wrong with your best friend dating your younger sister. It is up to them to find a new partner, and that is what is wrong.
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Let her know what is your friend's attitude towards other girls. Let her know the truth. If she don't listen, it is not your fault already. But start with asking your friend first and ask him not to lie to you. Tell your purpose. Tell him that you are not ruining what they had started but you just want to know the truth and save your sister.
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Whether there is something wrong with your best friend dating your younger sister depends on various factors, including the age difference, maturity levels, and dynamics involved. It's important to communicate openly with both your friend and sister to understand their feelings and ensure everyone's consent and happiness in the situation.
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Navigating situations involving friends, family, and potential romantic relationships can be complex and emotionally charged. Here are some steps to consider:

  1. Gather More Information: Before jumping to conclusions, try to gather more information. Pay attention to their behavior when they're around each other and observe if there are any signs of a romantic relationship. However, be careful not to jump to conclusions based solely on assumptions.

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I believe you should first ask your best friend if he is dating your sister, he should be open with you, if his answer is yes ask him how serious he is with your sister because you won't want him hurting your sister. Also ask your sister what is going on between the two of them, tell her to be open with you, tell her the truth regarding your friend with girls. Then let her make her decision, you have done your part.
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If you are feeling like this you should confront him just talk to him what is the matter it can be true or not if you want to find you need to talk . There us nothing wrong if your bestfriend is dating your sister but if he is a playboy you should be worried nothing is wrong in it.
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