Dear Tyler and Jay: What do I do if I’m in love with my best friend?

| April 6, 2023
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Spring has sprung at Hopkins! We hope you all had a restful Spring Break and that you are enjoying the warmer weather that we’ve been having. Springtime means new beginnings, a theme that’s reflected in the questions we got this week.

Q: Someone I thought was a close friend was demanding a lot of emotional energy from me. I told them that I couldn’t support them at the time, and they made personal attacks about my character and capability. I felt like that crossed a boundary, and I decided to address that. They then turned it against me by saying that my bringing up the matter was attacking them and that they felt uncared for. We haven’t spoken in months since. Am I the asshole?

A: First of all, kudos to you for establishing boundaries and being willing to sit through conflict. It can be really uncomfortable. But so can holding your tongue and sitting with resentment.

When resentment builds, it can affect the dynamic of the relationship with unhealthy actions like the silent treatment and passive-aggressive statements. When establishing boundaries, whether it’s time or energy boundaries or boundaries on what people say to you, the only thing you can do is state them. You can’t control how other people will react. However, there are some boundaries that must be respected, such as those around physical and emotional safety, including consent during intimate moments.

When it comes to potentially being an asshole when you set boundaries, it’s not what you say. It’s how you say it. Some people may state their boundaries in a cruel or manipulative way. Ones I’ve heard before are boundaries people express about their partner not talking to people of a certain sex or gender, which can easily slip into controlling behavior. I’ve also heard of people using the concept of boundaries to avoid being held accountable, even if their friend/partner is pointing out a problematic behavior or belief in a constructive way.

Again, I wanted to remind our readers that there are some non-negotiables like boundaries around physical and emotional safety, and around consent during sex.

Sometimes boundaries need a consequence to work. A sample script for this strategy might be: “Please don’t call me immediately after my class. I need time to relax before talking to others. If you call me, I won’t respond until tomorrow.”

But be mindful these consequences don’t slip into ultimatums. Ultimatums are more appropriate when a boundary is stated repeatedly and not respected, or if it’s a boundary about physical and mental safety and consent.

Some people can become defensive or offended when you establish boundaries. Maybe they have never been on that side of a boundary. Maybe they thought what they were doing was normal and healthy, and now they’re being told it isn’t. Boundaries are about the person setting them more than the person receiving them, so if you feel uncomfortable when someone sets boundaries with you, remember that healthy boundaries are ways a person is stating what they need to keep you in their life.

Boundaries can become toxic when they start to create a growing power imbalance. When one person asserts their needs over the other’s in a way that takes advantage of another’s vulnerabilities and controls multiple aspects of their lives, it can become problematic. It’s important that your boundaries come from a place of establishing general healthy dynamics in the relationship rather than controlling someone else’s behavior.

Based on what you shared, I think you’re NTA. I believe the way your friend reacted was more about being called out and not having the usual access they had to you more than anything else. I hope that this answer provides some insights on boundary setting that can inform future situations.


Q: What do I do if I’m in love with my best friend, but I don’t want to ruin our friendship?

A: A tale as old as time. I personally love stories like these because it’s beautiful to see a relationship develop over time into something more, or when you realize that your person was right there all along. From a pragmatic standpoint, I think you can and should look at this from two different perspectives to think about what’s best for you and how to preserve your friendship as much as possible.

Option #1: You tell them how you feel.

If you decide that you tell them how you feel, make sure you are prepared for your relationship to change in some way, shape, or form. Regardless of whether your feelings are reciprocated, your relationship is going to feel different because they either know that you feel more for them, or you pursue a relationship together.

If they do not feel the same way, respect their feelings and be intentional about setting boundaries for yourself and the friendship, so that you can move forward and feel secure being around them. You should also reflect on whether you need to take a step back from your friendship for a bit, just to ensure that you have the capacity to give the friendship the proper effort it requires!

If they share your feelings (yay!), then you should have a conversation about what you both feel is the most comfortable way to pursue a romantic relationship. Ask questions about any new expectations about how you show up for the other person, what would happen if the relationship happened to not work out, or what you envision your relationship to be now that you’re becoming more than friends.

Option #2: You don’t tell them how you feel.

You could also decide not to tell them how you feel because you value your friendship. This way, you are making a conscious decision to withhold your feelings to ensure that your best friend remains in your life. But you have to be okay with not telling them, if that’s what you choose.

If you don’t tell them, give yourself the proper time and space to process how you’re feeling and to let them go, so that you can truly enjoy being with that person and having a fulfilling relationship with them, even if it’s not quite the relationship you wanted. You might always wonder what if, but remember that you can always choose to tell them that you’re in love with them in a different time and space, if you’re ready or willing to.

I always think that it’s best to wear your heart on your sleeve and let someone know how you feel. Not only will you have an answer, whether it’s the one you want or not, but this way you can actually be present in whatever relationship you and your best friend have by knowing where you stand. Yes, your relationship is going to change, but that doesn’t mean it has to be ruined, especially if you put in the time and effort to maintain your relationship with them in a way that feels best for everyone. Whatever you decide to do, I hope it works out and know that whatever is meant to be will be!


Q: How can I tell my friends when I’m lonely without feeling like I’m emotionally manipulating them into spending quality time with me?

A: I think the answer to this question is centered around reframing your thoughts around this! It is completely valid to lean on your support system when you need it. But you’re right: there is a difference between guilting them versus opening up about your feelings and hoping they make the effort to spend more time with you.

Remember that sharing your feelings is part of having a relationship with someone else, so it’s okay to be vulnerable and tell them what you’re currently experiencing. To help reduce the feeling that you’re emotionally manipulating them, communicate that you are not putting an expectation on them to fix this feeling. Remove that pressure from the relationship, and then they can make the decision as to how they can best show up for you. I recommend having an open conversation with your friends about how to make sure the time you spend together is meaningful and fulfilling for everyone involved. By doing so, you and your friends can have an honest conversation about how you show up for one another and your expectations around friendship, so that everyone is on the same page and feels cared for.

If you are feeling lonely, I would encourage you to also lean into investing in your relationship with yourself. Do activities that make you happy, try new things, or incorporate self-care into your routine. You can also try to put yourself in social settings where you could meet new people, or find others with common interests. Sometimes the best you can do is just show up for yourself, rely on others when you need them, and know that you are never alone.


If you are interested in learning more about healthy relationships or gender-based violence prevention, April is Sexual Assault Awareness Month. For the entire month, the Gender-Based Violence Prevention, Education and Response Team will be focusing on sexual assault and gender-based violence prevention; consent and healthy relationships; supporting survivors; and promoting healing. Read this month’s calendar of events here and email [email protected] with any questions.

Keep sending in questions to Dear Tyler and Jay for all that you want to know about love, dating, and relationships!

Note: DT&J is intended to educate and spark discussion. The advice offered is intended for informational purposes only, and is not intended to replace or substitute for any professional, financial, medical, legal, or other professional advice. If you have specific concerns or a situation in which you require professional, psychological, or medical help, you should consult with an appropriately trained and qualified specialist. If you need help getting started, you can email [email protected].