Dear Millie,
How do you ask out someone who’s your friend?

“Friend to lover” tropes always sound like a good idea, but sometimes, dating your friends is a recipe for disaster. You put a lot on the line by pursuing a friend, so to lighten the load of this decision, take these factors into consideration. When addressing the idea of a romantic relationship, think about how long this person has been your friend. Also, consider if you truly think the two of you would work romantically. Friendships often don’t function the same way relationships do. If you have different standards, beliefs or ways of showing love, a relationship may not work the way you expect it to. Finally, before you begin strategizing, consider if your friend feels the same way. If they aren’t interested, pursuit may make your friendship awkward. At the end of the day, you don’t want to risk losing a friend over a relationship that may not work out.
However, if you feel there’s something between the two of you and nothing will be ruined, I think you can begin your plan of action. If the vibes are right and you know for a fact that this friend feels the same way you do, that’s great news, but don’t rush it. Your best approach will be to ease yourself into asking the hard-hitting questions. Make spending time with this person nonchalant because the more comfortable you are with them, the easier it will be to openly discuss your feelings. When you feel it’s appropriate, you can start getting to the big question.
When having a conversation about pursuing something more, approach the topic casually. Rather than admitting your feelings right away, consider asking how they feel about your friendship. This way, you leave it up to their interpretation, and the ball is in their court. If they bring up feelings, this gives you the perfect opportunity to ask the desired question of going forward with a relationship.
Since a friendship is ultimately on the line, patience is needed. There’s no sense in rushing anything since a connection is already established. When it comes to asking your friend out, pose the question open-endedly, similar to asking about their feelings regarding your friendship. I think it could be beneficial to ask how they would feel about the possibility of a date and if they would like to test the waters of something more. This way, you both can gauge how hanging out would be in a romantic way. From here, if the date goes well, it’s definitely a relationship to pursue, and if not, maybe you’re both better off as friends.
In the end, however, with a friendship, your best bet is to take it slow and steady. There’s no reason to rush anything romantically, so just enjoy the process. Collectively decide what’s best for both of you and be sure to communicate your comfort levels with each other. Wishing you the best of luck, and I hope to receive an invitation to the wedding!

Love,
Millie