Here’s How You Know It’s Time to Tell Him You’re Into Him

You have a friend you secretly love. You convinced yourself you had to behave like “just a friend” in order to keep them, afraid they’d walk away if they knew the truth because you were sure they’d never feel the same. That could be true — or it could be your low self-esteem making that assumption for you. What if, all along, they were also pretending to be only a friend? Should you take the chance and tell them how you really feel?
Today’s letter is from a woman who calls herself Selena. She writes: hi Anna — I need some perspective about the relationship I have with my neighbor. It began last year and has always been a friendship, but sometimes I wish it would become more. Other times I’m content just having his support; I don’t want to lose that because he’s one of the few friends I have. Last September a childhood friend of mine was visiting and we were swiping on my dating app when my neighbor’s profile showed up. We confirmed from his profile that he appeared straight and single. My friend urged me to ask him out, so that evening I knocked on his door and invited him to go thrifting. It felt terrifying — I worried he’d make an excuse or flat-out refuse — but he said yes, which felt amazing.
That same night he texted to ask if it would be okay if his friend Sarah came along. I remember feeling disappointed because I’d half-hoped that outing might be our first actual date, though I never explicitly framed it that way. I agreed anyway, trying to act cool, and briefly thought maybe I could gain two close friends instead of one boyfriend. On the day we met, though, it was just the two of us. I asked where Sarah was and he said she wasn’t coming. We had a lovely time, and when we parted he asked what I was doing that weekend and whether I wanted to hang out again.
I should add that I haven’t seen him with other women since then. He has a few female friends but rarely mentions them to me; he talks about his guy friends more. Apart from one brief time I saw him with a woman at work — and asked for his number then — I don’t know if she was a friend or a date. I’ve not noticed any women in and out of his apartment. He’s only had two relationships: a high school girlfriend and a college girlfriend who cheated on him, which hurt him deeply. It took time to understand him. He’s not flashy, relentlessly charming, or classically handsome — he’s sweet, quiet, simple, relaxed and a little reserved at first. For months I mistook his calmness for lack of interest; now I recognize that’s just his way of being — he isn’t performing for anyone. He’s not my usual type physically, but the more I know him, the more attractive he becomes.
It’s been a year and he’s become an important part of my life. He’s done incredibly thoughtful things for me: he walks with me to the gym, supports my efforts to get healthier, we have weekly dinners, see movies, text almost every day, and sometimes he sends unexpectedly sweet messages that brighten my whole day. Apart from my parents, he’s the only person who got me a Christmas gift — my parents gave me cash to spend, but his present involved real thought and came with a touching note I reread often. One detail of that note used the word “friendship.” You might think that’s obvious: he’s telling you you’re just friends. But I’ve used the word “friendship” too while we were getting to know each other, out of my fear of rejection and abandonment. I know I shouldn’t have done that, but I did. So I don’t know whether he uses the word because I used it first, or because he feels the same insecurity. I can’t remember who “friend-zoned” whom. Did one of us do it on purpose? Did either of us mean it? I know I didn’t. I struggle to share my true feelings.
We get along so well and hold similar values about the future: both of us want children and prefer a less materialistic, more sustainable life. We joke about one day running a business together and dream about our future houses — saying things like “mine will have this,” and “oh, mine will have that” — and even imagine one of our houses sitting on the river. The problem is, we say those things but neither of us takes the leap to make them real. I’ve watched many of your videos and can see where I went wrong, but I still don’t know how to steer this back on course. I love whatever this relationship is, but I hate the uncertainty. Maybe it’s obvious to him, but I suspect he’s confused too. I can’t tell whether his texts are friendly or romantic. I don’t trust my own ability to interpret them: if he texts “hope you have a great day,” my lonely, romantic brain hears, “he’s thinking of me and loves me,” but it could simply be friendly kindness. I cherish him so much and feel lucky to have him, yet perhaps the truth is he’s just being a caring friend.
Your videos encourage stepping out of fantasy and into reality, because that’s where genuine, right relationships live. I’ve received so many mixed signals from him and given him many mixed signals in return that decoding the whole mess feels impossible. I could win Olympic gold in the mental gymnastics I’ve done over this. Now I feel too deeply invested to tell him and risk creating awkwardness with someone I see daily and who is important to me. At the same time, I don’t want all my emotional energy tied up in someone who can’t imagine a future with me. I don’t need him to commit tomorrow — I just want to know whether we’re heading in the same direction. Sometimes, when I feel confident about us, I delete my dating app. When I feel unsure, I reinstall it, look at other options, remind myself I love my friend more than those other guys, delete the app — and then the smallest thing makes me question everything and I put it back. It’s a silly, repeating pattern but it shows how my mind works. Can you suggest any subtle ways for me to discover how he feels without fully revealing my own emotions? Could I ask him whether he’s been seeing anyone, or how his dating life is going? At the start we used to discuss those topics but haven’t in about five months. Is there a way to learn his feelings without endangering the friendship? What should I do next?
Selena — your letter is wonderful. Many people might say, “You’ve been friend-zoned, he’s told you,” but I see things differently. You seem to be in a deep, genuine friendship and there are signs that he might feel similarly. I don’t think there’s a clever, covert way to reveal the truth; you basically have to lay your cards on the table. Because this friend matters to you so much — he’s basically one of your only close friends, someone who gives thoughtful presents and who texts you every day — you should consider the possibility of hearing “no” and be emotionally prepared for that outcome.
You’ve been friends long enough for this to be a real, solid connection, and you shouldn’t keep pretending your feelings are something other than what they are. You can, however, keep the conversation light and low-pressure when you disclose — that’s what disclosure is called — and the relationship you describe has grown out of genuine friendship, which is a lovely foundation for romance if that’s what unfolds. If it doesn’t become romantic, I wouldn’t want you to lose this friend. Your friendship seems sturdy enough to survive an honest conversation, and I’d give the odds about fifty-fifty that it will. On one hand, he would likely have acted if he had romantic interest; on the other, he may be mirroring your use of the word “friendship” out of the same fear of rejection, which means he might be open to more.
You’ve already intuited much of this. Given your history — therapy, and a mother who was dismissive when you disclosed sexual abuse — it’s understandable why you’ve become guarded and somewhat frozen in this part of your life. That experience explains a lot about why you haven’t been kissed or why you hesitate to start a relationship. Still, from everything you’ve said, this man clearly cares for you, at least as a close friend. You’re a good, whole person who could have a healthy romantic relationship, whether with him or, if not, with someone else in time. The healthiest next step is to tell him how you feel.
You described the moment he slid a note with his number under your door, simple and genuine; you liked that he wasn’t putting on a show. Those are positive qualities in a partner or a friend. When you asked him out, he said yes, and your reluctance to label it as a date probably came from that frozen place that finds beginnings hard to initiate. Telling him will start the thawing. The episode where he offered that his friend Sarah might join and then she didn’t come could have felt like a friend-zone move — but then she disappeared from the picture entirely. He’s relaxed and reserved, not trying to prove himself, which you find attractive. The Christmas gift and the sweet note are strong clues; when someone invests thought and writes something tender, it’s meaningful. Yes, the note used the word “friendship,” but you have used it too out of fear. I’d split the odds — he might be repeating your phrasing, and he could be open to more.
When you tell him, keep it straightforward and calm rather than dramatic or melodramatic. You don’t need an overblown preface. Try something like: “There’s something I want to say. I feel a little scared and embarrassed because I don’t know how you feel, but I want to be honest: I have feelings for you. It’s more than friendship for me.” See how he responds. If he says no, you can reply: “I’m glad you told me. It hurts a bit, but I care about our friendship and I’ll do my best to adjust.” Pay attention to how you cope afterward: if being around him feels unbearable and you’re constantly upset, you might not be able to remain close right away. That is a risk you take by telling him. Yet carrying on forever pretending to be content as “just friends” when you love him will freeze a huge part of your life. Someone who shares your affection and values is a rare find; don’t let this chance pass without being honest and giving the relationship a real shot.
It sounds like you two share similar ideals — the business, the houses — and while people can say those things lightly, your descriptions don’t suggest manipulation. It may simply be that he’s not perceptive of romantic signals and has unintentionally put you in the friend zone. Waiting for a relationship to reveal itself without directness is risky; if a connection is meant to develop, there are many ways it can show up, but nothing can move forward unless people are honest. All the overthinking and mental gymnastics won’t create reality. You worry that asking now will make things awkward — yes, it might sting and feel strange at first if he isn’t interested, but your friendship seems real enough that it could survive. For those reasons, I recommend you tell him now, intending to preserve the friendship whatever the answer.
Finally, if anyone watching wants support getting ready for a healthy relationship, there’s a free download available right here. See you very soon [Music]