I can’t tell you the number of times I’ve opened my Instagram feed to see couple’s anniversary posts. While reading them, there is always a certain sentence that stands out for me: the one where they thank their significant other for “being their best friend.”

Don’t get me wrong. I am such a proponent of dating your best friend, especially if you are best friends before it turns into something more. Establishing a friendship before romance can be essential in creating a baseline for trust, loyalty, and overall strength in a relationship. If you already enjoy this person’s company so much and know you can count on them for a good laugh, cry, and anything in between, then once you shift into a relationship, that foundation is already there, which is key.

What they don’t tell you, though, is that if and when the relationship does end, the shift and moving on is made even more difficult. When you break up with your boyfriend or girlfriend who you also consider your best friend, you find yourself grieving two relationships: both a romantic one and a friendship.

The most ironic part of all this is, that during this breakup, the one person you want to talk to and console you, is the same person you are trying to get over.

I think you all can see the issue I am trying to pinpoint. When you date your best friend, you risk potentially losing not just a romantic relationship, but a friendship too. Often times, couples say they’ll “stay friends”. To me, this seems too difficult to maintain, at least in the beginning.

Friends tell each other things.

Do you really want to hear about if your ex has met someone else or how they're thriving if you’re still struggling to move on?

From breakup on, there may be a certain line or boundary you can’t cross. Conversations can become superficial if both of you guard the words you say, and try to seem better than you are, or leave out bits of information because you don’t want feelings to get involved or people to get hurt.

You may say you want to stay friends, but if you haven’t completely moved on yet, staying in contact may be too much of a trigger and may halt the healing process.

This does not go to say that I do not think it is possible. However, I think getting to the point where you feel healthy enough to engage in a friendship with your ex again takes time. It may require distance and a focus on yourself, a chance to regroup. This will be hard. It’s strange going from hearing everything about someone’s day to nothing at all. It’s strange not knowing if it’s safe to reach out if it’s healthy or wanted by your ex. Still, the space is so important, because without it, you may find yourself holding onto a lingering hope that things can go back to the way they were.

The space is crucial for finding closure within.

Another thing that makes things hard, is distinguishing whether you are missing your ex romantically or simply as a friend. Dating your best friend means feelings get muddled, and sometimes you can’t tell which is which.

Again, I think it’s great to date your best friend. At the same time, I think that it is also important to reach out to other people you can trust while you are dating, to maintain your other relationships and friendships. I am forever an optimist, but I am real enough to recognize that we need to guard our hearts, and doing this means filling your life with love from many different people, not just one singular person.

If we decide to fill our lives with love, both in a relationship and in other friendships, then the loss of a relationship will not be so daunting, because our hearts are already full.

Keeping the mindset of filling your life with love, all types of love will help you realize that you can love a person in many different ways. Even if you and your ex have lost whatever you had romantically, there is a chance you can, with time, maintain a friendship. And there’s a chance that this won’t happen. Let things be as they will.

So yes, date your best friend. But recognize that moving on may be more difficult, and it may take some time before you feel able to call your ex a friend again. Things may never go “back to normal,” but who needs normal anyway?

Always remember you are loved, lovable and loving, and the world is your oyster.

Talk soon,

Sam