Having feelings for a friend can be both exciting and terrifying.

It feels familiar because they’re someone you’ve already known for a while. They’re someone you enjoy spending time with, someone you can trust, and maybe someone you’ve shared a few of your closest secrets with.

Maybe some unexpected romantic feelings are now starting to surface when you’re around her. After all, you’re most likely compatible because you’ve been around each other for a while now and each time you see her those feelings of fondness grow more and more.

I’ve had my fair share of crushes on friends over the years. Sometimes I’ve been able to ask them out successfully. Other times, they’ve turned me down, but we were still able to preserve the friendship.

It’s totally natural! With such a mixed group of friends hanging out and traveling together, it was only a matter of time before some of us began to develop feelings for one another.

But, what if it doesn’t work out? Are things going to be awkward now? Is it going to ruin your friendship with her?

Today’s newsletter is about how to ask out a friend and give yourself the best chance of success, while also keeping your existing relationship with her intact no matter how it turns out.

Should I ask my friend out?

Probably! But there’s a few things to consider first.

Is it possible that they feel the same way towards you?

Maybe you’re feeling emotions toward her because you’re unconsciously picking up cues that she’s interested in you!

• Do you see her subtly taking up your personal space when you’re together?
• Perhaps she’s acting shy, asking more personal questions, or laughing at your jokes more?
• Is it possible that she’s recently gone through a difficult life event (a breakup, job loss, etc.) that’s made her rethink the way she feels about you?

Try spending some one-on-one time with them to get a sense of how they feel. Are they showing any of those signals from above? That might be a good sign!

What do your other friends think about it?

It’s possible they know something that you don’t that can help you win her heart! Over the years, I’ve had mutual friends in my groups come up to me and say “Steve, you know Chloe’s had a crush on you since forever” or “Elizabeth just broke up with her boyfriend and she’s been asking about you a lot”.

But what if you’re a little less fortunate and something like this doesn’t just fall into your lap? Show some initiative! Approach someone you both know and ask what kind of things she likes to do. You might try asking your mutual friend,

“Hey, I’m thinking of asking [her name] out to the carnival. Do you think she’d like that?”

And they might tell you,

• “Yeah that’s a great idea!” or,
• “Actually she’s been hoping to check out the new board game café that just opened up across the street. Maybe you should take her there.”

Just make sure that you trust the person that you’re approaching for advice. Some people love to gossip! The last thing you want is for rumors to reach her before you’re ready to ask her out.

Does she have healthy attitudes around dating?

You might find yourself having feelings for a friend after discovering you have a lot more in common than you previously thought. But if you’ve seen unhealthy behaviors from her in her other relationships then that’s not likely going to change when she starts dating you.

One of my friends who is chronically single seems to enjoy “testing” the men she goes out with. She pretends to pull away and then waits for them to chase her because…it proves they truly love her, or some crap like that. She’s also the one in our friend group who seems to struggle the most with relationships. I’m sure that’s just a coincidence.

Also, think about any differences in beliefs or personalities that might cause friction between the two of you. Is she religious and you’re agnostic? Perhaps she’s a cat person and you love dogs? Does she pour milk before cereal?

It’s easy to overlook such differences when you’re just friends and have separate lives. When you start going out with her, however, those differences are going to follow you home. Possibly for the rest of your life.

Is she already in a relationship?

Sorry, the answer is no. This is still true even if it seems she likes you but has a boyfriend.

You’re not going to win her over by proving that you’re a better boyfriend than the one she’s currently got. She’s not going to break off from her existing relationship because you persisted after her.

Why would she?

She gets to have both 1) an actual boyfriend and 2) a pseudo-boyfriend (i.e. you) who gives her the benefits of having another romantic partner, without requiring any commitment from her.

In other words, she gets to have her cake and eat it too!

One of my favorite nerd-dating-coaches, Rami from Gutsy Geek, wrote a viral article on exactly why this is a bad idea. (Sadly, I think he’s retired from dating advice. I’ve reached out to him asking if he’s going to keep writing but he’s stopped responding to messages. Ah, well.)

When should I ask out a friend?

So, you went through that list above and you still feel good about asking her out?

Awesome! I’m rooting for you!! I’ve done this successfully in the past — watch the video to learn the true story of how I asked out a female friend and ended up in a relationship with her.

Now, the best time to ask her out is as soon as possible. Wait too long and it’s going to backfire in your face. Here’s why:

She may question your intentions if you wait too long

Some men think that by being “friends first” you’re building the foundation of a later romantic relationship.

That’s wrong.

If you try and be friends with her first, you’re not setting yourself up for any relationship other than a friendship.

Now obviously I’m not talking about someone you happened to be friends with first and then later developed romantic feelings for. That’s different. That’s OK. And I have seen that work successfully.

But if you end up harboring these feelings for several years before asking her out, you start to look like one of those other chumps trying to pull off the “friends first” strategy. She’ll wonder if you truly saw her as a friend during the time you spent together, or if it was just a way for you to try and get into her pants.

You’ll want to get her answer sooner rather than later

It’s really easy to procrastinate and put off talking to her about your feelings for as long as possible. We know that we “should” talk to her about it, but there’s also a lot of discomfort involved, so it’s easier to talk ourselves out of it.

I always did that. Because I wasn’t sure how to handle either answer.

If she said no then…how would I get over that? And if she said yes…I wasn’t sure how to handle that either.

That’s where one of my biggest regrets comes from.

A long time ago, I had a crush on a female friend named Joyce. Instead of asking her out, I let those feelings fester into an obsession. Sometimes I’d have trouble eating because I was thinking about her too much.

My other friends saw that my obsession was becoming unhealthy. They tried to talk me out of it and reassure me that “there were plenty of other fish in the sea”. I didn’t want to hear it. I’d built up a mental image of my friend and “fallen in love” with that one – a completely different person from the real Joyce.

I’d built a prison inside my own mind. If I asked her out and she said no, that meant breaking up with the imaginary Joyce who lived inside my head. And if she said yes…well, she’d still turn out to be a different person from the one I knew and that would be hard too.

I was screwed other way. And my actions ruined a genuine friendship.

Guys, rip that bandage off sooner rather than later.

(And yes, after typing that out, I do realize it sounds like the plot of a certain 2025 horror film. That wasn’t on purpose. Also, Bear was the true villain and it’s disturbing how many people think he wasn’t.)

Some other chump might ask her out first!!

Le gasp. NO!!

That female friend you have feelings for? Some other chump might also feel the same way about her.

Worst of all? If she doesn’t know how you feel…she might say yes to him. And then your friendship is going to be ruined anyway because you get a backseat to them being a couple, even though you know you should “be happy” for them but you just can’t.

Don’t let some…umm…guy who’s the opposite of “Chad” take your girl away!

(Wait, who’s the opposite of “Chad”? One sec let me Google that…)

(Google says Melvin. We’re going with Melvin.)

Don’t let Melvin go out with your friend. That should be YOU, dammit!!

Here’s how you go about asking her out.

How to ask a friend out on a date

Keep in mind that everything below is just a suggestion.

You know your friend better than I do! If your experience tells you that one of my suggestions clashes with how she would like to be asked out, then you should probably listen to your intuition.

Here’s what I would recommend.

Figure out when and how you’re going to ask her

Traditionally, I’ve always recommended asking her out in person or over a phone call after getting her number. But you and your friend already know each other, so asking her out as if she were a stranger might be off-putting.

Think about how you typically invited her to places back when she was just a friend. Was that in-person? Did you call her up? Or, maybe it was just a simple casual text message? If most of your communication was done over text message, then I’d ask that friend out on a date over text. (Just be sure to ask her out privately and not in front of your other friends, or she might feel pressured).

Ask her out to a specific time and place. Naturally weave the invitation into the conversation if you’ve decided to ask her out over the phone or in-person. Keep it simple and don’t make it seem like a big deal.

Letting her know about your feelings

At this point it’s highly possible she “gets the idea” and realizes how you feel toward her. A single guy asking a single girl to a one-on-one activity? She might connect the dots and understand it’s more than a platonic invitation.

If so, lean into it! Be upfront and tell her YES if she asks whether you’ve got feelings for her or if this is an actual date.

But if she hasn’t put two-and-two together yet then you’ll want to let her know on the date itself. Avoid “love dumping” all your feelings on her or you might scare her off. Basically, you want to convey the message like,

“Hey [HER NAME], I’m telling you this because I care about you and want to be honest. If you don’t feel the same, I understand and that’s totally OK. We’ll still be friends like before, no matter what happens.”

Asking out a friend without ruining a friendship

Hopefully they respond positively! Maybe they’ll tell you that they felt the same way *fingers crossed*. Or, if you ask them out, they ask if it’s an actual “date”, you say YES, and they still agree to it, then it’s a safe bet they’re open to a relationship.

They may also need some time to think about it. It’s a heavy decision for her that sends a shockwave through all areas of her life. If she brings up any concerns, listen to them! Don’t be surprised if she suddenly needs cuts the date short and tells you she needs to think it over.

Give her the time and space she needs to process everything. Even if she’s never thought of you more than friends before, it’s possible that she may realize she’s attracted to you as well after thinking it over!

But if not, respect the way they feel and avoid pressuring them to change their mind. Tell them that you’re still happy to be their friend. Give everything a little bit of time to settle if it feels awkward at first. Rejection stings! There’s no “ifs, and, or buts” about that. So, if you need some time to yourself before you’re ready to face everyone again, that’s OK too!!

Asking out a friend is scary. If you’ve started to notice romantic feelings towards her, I’d let her know as soon as possible. Whether she says “yes”, “no”, or “maybe”, now you know how to handle it. The only way to fail is if you do nothing and Melvin gets to her first.

Wishing you the best of luck!!

…And seriously, for the love of all that is good in the world – PLEASE ask her out before freaking Melvin does.