Best Boy/Friend




Q: Hi Lisi! I have a question I’ve been wondering about and I feel like you would give a great answer to. How do you tell a certain guy you like him? i’ve been best friends with this guy for years and I think it might be turning into something more, but it seems like we’re both afraid to cross over that barrier and see what the other is thinking. I realize telling him and finding out he’s not interested could ruin our friendship but I’m ready to take the risk. I’m just not sure how..Any words of wisdom? Thanks! you’re the best!
– Sara

Sara, this is a great question I’m sure a lot of readers have wondered themselves. I don’t blame you for being curious about whether or not your close relationship with your best guy friend could turn into something more. But there are a few things to keep in mind before taking the leap and potentially losing the connection you now have with him.


Has your friendship changed in ways that make you think your guy friend is romantically into you? Think back to his words and actions. Does he worry about and consistently consider your feelings, act protective over you when it comes to other guys you’ve been interested in, and show you his emotional side? These might be signs he’s into you as more than a friend, but if he’s always talking about your hot friend or treats you just like one of the guys, you may want to stay in platonic territory.


Guys are repelled by complicated dating situations, so if you choose to start a conversation about where each of you stand do your best to keep things light and easy. You’ll need to be a little bit vulnerable to open up a dialogue about your feelings, but there are noncommittal ways of doing this so you can save as much face as possible if things go awry. At a time when you’re joking with your guy friend or having fun together, find a way to test the waters. Maybe you’re watching a funny movie together where the central characters have a situation similar to yours and end up dating and falling in love. Throw out a “Well this really is fiction because friends falling in love almost never works out. What do you think?” If he’s on the same page as you, he’ll see this as an opportunity to explain why friends turning romantic can potentially work. If he’s not thinking of you in the romantic sense, or truly believes dating a friend is a recipe for disaster resulting in the loss of a great friendship, he’ll be sure to express that too.


You mentioned you are at a place where you’re ready to risk possibly ruining the friendship with your guy friend in order to tell him how you feel. It’s completely possible to share your feelings with him and keep the friendship strong even if he’s not thinking of you in the same way, though it will probably shift the connection you two have for a while. You won’t necessarily lose him altogether, but you have to keep that possibility in mind. It would be easy for me to say that keeping the friendship in tact is the wisest choice in your situation, but I know it’s not always realistic. If you are certain you’ll be able to handle losing the friendship or making things awkward to the point of changing your friendship dynamic forever, then take a leap and see what happens. You already know the worst case scenario, but at present you don’t know what the best case outcome might be. Stay cool, keep things light, hope for the best but prepare for the worst. Good luck!!!

I’m loving all the crush questions that have been submitted lately but next week we’re going to shift gears a bit. Send me questions you have on writing, school or social woes. Can’t wait to read your thoughts.




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  • Anonymous Fakename says:

    How do I get my crush to notice me? Has that been asked already? Or is it too short?

  • Ehma-yes! I wish you could do a post all about Massie, because she’s my favorite, obviously!


  • Andrea says:

    I’m sure you’re sick of Clique-related questions and probably have answered this before, but I would like to know if there will ever be a “where are they now?” type of Clique book in the future. There are so many unanswered questions that we were left with at the end of A Tale of Two Pretties, like “Did Massie start a new clique at her new school?”, “How did Alicia handle taking over the PC?”, “Did Massie come back to visit in the summer?”, “Did she stay in touch with the PC?”, “Did the PC stay together once Massie was gone, or did they move on to new friendships?” I think it would be interesting to see the PC in high school or college, to see how they have changed (or not changed). Meg Cabot is writing a similar book for The Princess Diaries series, set 10 years after the last book where Mia is getting married. I think an adult version of the Clique book, set maybe 5 or 10 years after to see where the PC is would be really neat. Many of the Clique fans started reading the books in middle school and are now college age. Many of us, including myself, have grown up with these books and like to feel as though the PC has grown with us too.

    • Melanie says:

      I agree with you… I love the Clique, Babysitters Club, and The Princess Diaries. And I always wish there wold be a after book.

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