In spite of the wisdom that comes with experience, we know love doesn’t necessarily get any easier with age. It can get even more difficult if you’re considering that most classic of conundrums: turning a friendship into something more. While we know the risk of losing a friend can be daunting, we also know what a uniquely rewarding experience dating your best friend can be. If you’re considering asking someone out — and if that someone is already your friend — keep these eight things in mind to minimize the risk and maximize your chance at love.
For better or worse, being great friends doesn’t always translate to a working romantic partnership. Is there a level of trust there that extends not only to confiding in each other regarding your frustrations at work but also to a real emotional vulnerability? Does one of you tend to seek constant companionship in a relationship, while the other prefers more independence? It can be easy to overlook these basics when you already work so well as friends, but it’s important that you both be honest with yourselves and each other about what you need from a partner and what your relationship goals are when considering dating a friend.
The question itself is simple: Does your friend return your feelings? Determining this, however, can feel like a minefield of mixed signals. Many in this situation will resort to flirting to see if their friend returns the playful attitude, which allows them to write off any rebuffed come-ons as mere joking. This roundabout approach, however, is anything but guaranteed. Flirting comes more naturally to some than others, and its presence — or lack thereof — may say nothing about the level of actual attraction.
If you believe there’s any chance your feelings might be returned, being direct is the surer, more mature way to broach the topic. It also eliminates the drawn-out dance of uncertainty that could otherwise go on indefinitely.
If you’re considering asking someone out who is part of a larger group of friends, give yourselves some space to see how it works without everyone else around. Spend some time with just the two of you before moving into an explicit dating scenario, and be prepared for the dynamic to change without the energy from the rest of the group. If you do progress into a relationship, know that the group dynamics will likely change as well, and try to avoid putting any mutual friends in the middle of your conflicts as a couple.
You may feel that a difference in values — whether it’s in regard to family, lifestyle, or even your general outlook on the world — isn’t an issue when you’re only friends with someone. It becomes a much larger problem, however, when you’re considering them in light of a romantic relationship. This can be especially true if your friendship is centered around one particular activity such as playing a sport or taking advantage of nightlife. While it’s easy enough to enjoy someone’s company over cocktails, you want to be sure you have more than only a shared appreciation of happy hour in a life partner.
There are two crucial aspects to consider when it comes to communication and dating a friend. How well do you communicate as friends? Do you find yourselves easily understanding the other’s perspective, or is there a lot of misinterpretation that happens? Any difficulties you have in this department will be magnified in the context of a relationship.
If you do decide to try dating, communication at every step of the process becomes even more crucial. Because you already have a routine established with them, it will be easy to make assumptions regarding where you both are. When you begin dating a friend, however, you need to be extra clear that you are both on the same page.
Given that you’re already close — and that a romance between friends often feels like it’s been a long time coming — it can be tempting to jump into things. Recognize that adapting to each other in your new roles will take time, and resist the urge to rush. Given your previous friend status, you may find your relationship progressing through its various stages in a different way than you’re used to.
Understand, too, that there will likely be moments of awkwardness as you transition from pals to partners. It doesn’t say anything about your relationship, either good or bad. All it means is that it’s changing, which is inevitable when dating a friend.
When dating a friend, it’s easy to feel more pressure than you otherwise would to make it work. After all, if you were willing to risk a friendship, you must have been convinced they were your soul mate, right? Add in mutual friends egging on your new romance, and you may end up feeling like your relationship has to succeed no matter what.
While taking things slow is one strategy that will help you avoid feeling like you’re on a runaway train, it’s also crucial that you and your friend be honest about what’s working and what isn’t. Even if you both entered the relationship with the best of intentions, it’s possible you aren’t right for each other — and that’s okay. At the end of the day, you want what’s best for both of you, whatever that is.
If you reveal your feelings to a friend and they don’t return them, don’t take it personally. Their rejection isn’t of you as a friend, and there’s no reason you can’t continue in that capacity. Do be honest if you need space to move on yourself, but don’t mistake their lack of romantic interest as a lack of appreciation for you in their life at all. There’s no need to be embarrassed, either. Confessing your feelings, whatever the outcome, is a brave move, and having certainty on your status beats living in limbo only to be disappointed years down the road.