How do you know when to tell someone you love them?

You know what’s amazing? Being in love with someone. Maybe you don’t believe in love, or being in love, but I do, and I think it’s pretty damn great. Loving family and friends is cool and all, but romantic love is just so goddamn wonderful isn’t it? But, you know what can be incredibly awkward? Telling someone you love them for the first time.

Have you ever told someone you love them, or are in love with them, and had that feeling not be reciprocated? Well, I have. I’ve also been on the other side of the table, and it is awkward. SO AWKWARD. That said, it can potentially be kind of amazing. So, how do you know when to tell someone you love them?  I can’t tell you for certain how to figure out when you should bring it up, because that will differ from person to person. What I can tell you is how to tell if you’re ready to tell someone you love them.

1. Be prepared for a bad answer.

While a lot of people will want to hear that they are loved, not everyone is going to react in the same way. Telling someone “I love you” for the first time can garner a lot of different reactions. In a best case scenario, they’ll reciprocate your feelings and you’ll live happily ever after. It’s also possible that the person you’re telling is just not in love with you right now, and may never be. It’s possible that telling them you love them is going to create a critical decision point. They may decide to leave because they don’t love you, or you might decide you want to end things. They could also just not believe in love, or not be in love with you yet but willing to wait and see. There are lots of ways telling someone you love them can not go in your favor, but in my own personal experience the worst reactions I’ve had were:

  • I was broken up with immediately after
  • She suggested a “break” and never ended the “break”
  • She said “you don’t really mean that”
  • I was told that I said “I love you” too early and ruined things

If you’re not prepared to potentially hear any of those things, or worse, you might not be ready to say “I love you”. It’s a high-reward move, so you have to know and prepare for these sort of high-risks.

2. Be realistic about what saying it will mean.

Saying I love you is all well and good, but it tends to change things between people. Even disregarding the potential bad that can come of it, the first love declaration is a milestone, and it may precipitate some changes between you and your partner. In a previous relationship, it took me something like 5 months of dating, to say I love you for the first time. This may be unique to that situation, but I knew that once I said it, I would need to do the following:

  • Enter into a committed, monogamous relationship
  • Discontinue any and all dating apps/sites

Maybe that’s why it took 5 months to say it, but that’s a whole other story. The point is, you need to figure out what saying “I love you” will mean for both of you. It doesn’t always mean entering into a monogamous relationship, but it might. It doesn’t mean you have to discontinue your Tumblecupid accounts, but it might. It might mean a lot of different things, and you have to figure out what it will mean to when you say it, and be realistic about whether or not you’d be ready for what expectations may come next. If you’re in a relationship or dating, it might mean one set of things. If you’re not currently seeing them romantically, if you’re in love with a (currently) platonic friend, it might mean something else entirely. Saying “I love you” to a friend who you’re in love with brings a whole different sort of changes and trust me, you still need to be realistic about what it might mean to both you.

3. Are you sure you love them?

I’m not saying you need to go through life with 100% certainty about how you feel about every single person you meet, but you should be pretty close to that when it comes to telling someone you love them. No one ever wants to hear “Actually, just kidding, totally don’t love you. Backsies?” so you want to do your best to avoid that down the road. I’m not saying that your feelings can’t change, people fall out of love everyday, but at the very least you should be mostly certain, let’s say something around 85% or more, certain that you love this person. Things change, and people change, and some people will never be 100% about just one person, but at least have the decency to be able to say that you’re almost 100% certain you do love this person. Telling someone you love them holds a lot of weight, whether they agree or not, and you want to try to be as honest as possible when it comes to love. Basically, don’t tell someone you love them unless you really mean it.

4. Ask yourself, one last time, are you ready to do this.

Are you prepped for the worst? Do you have a good idea of what saying it will mean for you and the person you love? Are you sure you love them? Can you say yes to all three of these questions? Congrats, you’re almost done! The final step is…

5. Say the words.

No more to it than that. Take the leap and hope for the best. You’ve prepared for the worst, so you’ll be mostly fine. Probably.

You might get rebuffed, you might be rejected, it might ruin things between you and the person you love. Or, your feelings might be reciprocated and you’ll feel like a million bucks. Honestly, I think that with the right person, in the right situation, and at the right time, the risk is always worth it. The right person, place, time, and situation will be different for everyone, so don’t worry about saying it too soon or too late so much as you should worry about the things I mentioned above. If the love is real, and you’re prepared for the worst, and you’re prepared for what might change when you say you love them, take the leap.

Good Luck Out There.

Demetrius Figueroa

Demetrius is a sex, dating, and relationship writer based in Brooklyn.

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