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If he's cool with it But it is a good way to f up a friendship. Scott , May 12, It speaks highly of your character that you sought to first gain the approval of your friend; as it is his sister. The fact that your friend is also okay with it, speaks highly of your character, as well as the fact that you still feel weird about it. I question whether you believe you friend was being sincere when he said he was okay with you dating his sister?

If you question whether he was being sincere, then revisit the subject; as from my understanding you have some time before you actual would make the trip.

dating your best friend's sister

If you are not questioning his sincerity, then it may just take you some time to feel comfortable about the situation as, I'm sure you were aprehensive about the whole thing at first; as well as possibly being aprehensive in the past. If you have time, don't feel rushed to make a decision, whether it be for or against. Continue to talk to her if you are interested to gain a better perspective of whether or not the two of you are compatible.

Not saying it has to be marriage material, but it cannot be a hit it and quit it situation. And if you feel that your feelings are sincere, take the woman on a date. I have dated sisters of several friends. I did address it with my friends before moving forward, and I treat all sisters with respect. Things didn't work out in the end, but I kept my friends and gained their sisters as true friends. ResoluteProtector , May 12, Grapple, you realize everything you do and say infront of your bestfriend will be scrutinized.

Dating your best friend's little sister?

If you look at a girl, or comment about another girl it now takes on a new meaning. It's no longer "boys being boys", now its you disrespecting his sister. I married my best friends sister. Get to know her better through family conversations. Use discretion and don't be too nosy, as this could be a big turnoff.

However, you may very well get to know a bit about her simply by hanging out with the family and listening to conversations with and about her and her siblings. If you are at your best friends house for dinner and there is a conversation about a family vacation, you might listen for details about her experience of the trip.

  • 3 Ways to Ask out Your Best Friend's Sister - wikiHow;
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Get to know her better. For instance, if you know she practices Judo twice a week, you might ask her, "What do you like about Judo?

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And how is it different from the other martial arts? Find a place to interact with her. If you go to the same church, for instance, you may have an opportunity to ask her out after the service. If you go to the same mall to work, you might run into her in the cafeteria.

So, you need to think about possible opportunities to ask her out. Ask her out on a date. You need to be very specific when asking her out, so that she has something to respond to.

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For instance, you could ask her if she would like to go for coffee after class or if she is free to check out a movie on the weekend. I found an amazing coffee place on third street downtown that has this incredible Italian roast. I think you would appreciated it. Do you want to check it out on the weekend? We are thinking of making the day of it, maybe bringing a lunch and trying to get in three or four climbs. Do you want to join us? Try indirect suggestions to ask her out.

If you feel slightly awkward about asking her out directly, you could use an indirect method. I was considering a movie on Saturday night. Maybe you would like to join me after your study session? You might ask, "How are you feeling about your upcoming theatre production at Studio Y? But if you want to practice them some more, I would be happy to help out. Maybe we could grab a coffee and I could listen and give line prompts? Express how much you enjoy her company.

If you have the opportunity to go on the date, it is best to be forthright in expressing how much you enjoy spending time with her.

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Include your email address to get a message when this question is answered. Already answered Not a question Bad question Other. Tips Remember that if age is an issue in the situation, take it into consideration and be open about it with your friend and their family.