How to Ask out Your Best Friend's Sister

Co-authored by Imad Jbara

Last Updated: October 8, 2022 References

Experiencing romantic feelings for your best friend's sister can be awkward. Although there is nothing at all wrong with having such feelings, it can be a tricky situation to navigate. The keys to exploring such romance are trust, respect, good communication, and honesty.^{[1]
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Research source} To maintain your friendship and explore a possible romantic relationship, you should focus on figuring out your true feelings, building positive relationships, and expressing your genuine interest.

Method 1

Method 1 of 3:

Getting in Touch with Yourself

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Figure out your feelings for her. Since you do not want to compromise your friendship, you should start by figuring out how much you like her. ^{[2]
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Research source} Take some time to explore your feelings in a journal. How long have you had feelings for her? How would you describe your feelings? Reflecting on these feelings, take a moment to make sure you are genuinely interested in her as a romantic partner.
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Practice being yourself. Rather than trying to change into somebody you imagine she would like, simply be yourself.^{[3]
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Research source} Take a few minutes and reflect on the values and character traits that you hope to embody in a romantic relationship.^{[4]
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Research source} It is okay to take some time when exploring the possibility of a romantic relationship.^{[5]
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Work on being honest about your intentions.^{[6]
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Research source} For instance, if you have a few crushes at the moment including one for her but also for a few other people, you should be honest with yourself about these feelings before moving forward. Do you feel stronger romantic feelings for her than for your other crushes? By asking yourself such questions, you can make sure you are pursuing a noble path.^{[7]
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Method 2

Method 2 of 3:

Testing the Waters

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Consider expressing your intentions to your best friend.^{[8]
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Research source} If you are certain about asking her out, you should probably communicate this intention with your friend. You want to handle this situation delicately so that it doesn't seem like you are asking permission from your friend, which she might not like. At the same time, you want to be forthright with your friend. Be respectful and communicate your genuine intentions, so that your friend understands that you are serious about a romantic relationship and have genuine respect for their sister and the family.
- You might go for coffee with your friend and find a moment to talk about your feelings. For instance, you might say, "Since we went to that concert with your sister Sarah and her friends in July, I've been having some pretty serious feelings for Sarah. I haven't had these kinds of feelings for a long time, and they aren't going away. I wanted to let you know because I would like to ask her out for dinner." If your friend questions your intentions, try restating your genuine feelings for her. If they reassure you that everything is fine, then you know the conversation has gone well.
2
Develop a solid relationship with the family.^{[9]
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Research source} If you have mostly been hanging out with your friend and do not know the family very well, it is best to spend some time getting to know the family. By putting some good time into developing these relationships at the start, you will have a better chance of being seen as a good dating prospect.
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Get to know her better through family conversations.^{[10]
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Expert Source

David Kornel Z
Dating Coach
Expert Interview. 24 January 2020.} You can get to know her a bit better by developing a relationship with the family. 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.
4
Get to know her better.^{[11]
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Research source} You can start to get to know her better before going out on that first date by having conversations with her wherever you can and asking about her passions and hobbies.^{[12]
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Expert Source

Imad Jbara
Dating Coach
Expert Interview. 22 September 2021.}
- For instance, if you know she practices Judo twice a week, you might ask her, "What do you like about Judo? And how is it different from the other martial arts?" By expressing an interest in something she is passionate about, you can learn more about her life and her interests.

Method 3

Method 3 of 3:

Asking her Out

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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.
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Ask her out on a date.^{[13]
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Expert Source

David Kornel Z
Dating Coach
Expert Interview. 24 January 2020.} You need to be very specific when asking her out, so that she has something to respond to. 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.^{[14]
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- You might say, “I remember you saying you love dark roast coffee. 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?”
- For instance, you might say, "A few friends and I are going rock climbing at Echo point 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?"
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Try indirect suggestions to ask her out. If you feel slightly awkward about asking her out directly, you could use an indirect method.^{[15]
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- You could ask, “what are you up to this weekend?” She might reply, “I have a soccer game on Saturday afternoon, and then a study group. I'm not sure yet what I'm doing afterwards.” If she says something like this, you could then say, “That sounds fun. I was considering a movie on Saturday night. Maybe you would like to join me after your study session?”
- For instance, you could also find an opportunity to help her with one of her projects. You might ask, "How are you feeling about your upcoming theatre production at Studio Y?" If she says she is worried about her lines, you might say something reassuring like, "You work so hard on them, I know you'll be great! 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?"
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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.^{[16]
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Warnings

You should be a good friend and tell them as soon as possible, and if your lucky, they will try to help you two get together, and remember, friendship comes first

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Be aware that the person may say no, and be prepared to accept the consequences of "making a move" on your friend's sibling.

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