5 Important Things To Consider Before Trying To Date Your ‘Friend’

It’s complicated.

So you have this friend. Lately, you’ve been starting to feel a little more than platonic. He’s funny, sexy, and you already have so much in common. What could go wrong? Take it from me. I’ve crossed that line with a few of my friends and it’s either led to a relationship, fizzled out or ended very very badly. My advice? Consider the pros and cons before you take a cue from Demi Lovato and “ruin the friendship.”

1. Pro: It could turn into a relationship.

This does happen! Once you see someone in a different light, everything can change. Your goofy drinking buddy can turn into your other half. A solid friendship lays down a strong foundation for something more.

My current long-term relationship started out as a friendship. I became friends with my co-worker when we were both casually seeing other people. Fast forward a few months and we were both single at the same time. Everything kind of just fell into place and we’ve been together for almost four years. A friendship turned romance can lead to the most meaningful relationship you’ve ever had, if you take the chance.

2. Con: It could end your friendship.

About 85% of relationships end in a breakup. Clarify whether you’re just hooking up or if it’s a fling that could lead to something more. Clear boundaries are key. There’s nothing worse than if one person catches feeling that the other doesn’t reciprocate.

I went through a similar experience my freshman year of college. I had just gone through a breakup with an on again, off again high school boyfriend when I began casually hooking up with my best friend. He thought it was going to get serious, and I wasn’t in the right head space to give him what he needed. I led him on because I didn’t want to hurt him, but that backfired. After a while, he decided it was too hard for him to go back to being strictly platonic and ended our friendship. What’s even more painful than losing your SO? Losing your best friend in a two-for-one special. If you’re not on the same page, then don’t take it to the next level. Period.

3. Pro: You already feel comfortable.

When you feel comfortable with someone, being with them will feel right. You don’t need to pretend to be anything other than yourself because they already like you for who you are. Support and acceptance right off the bat?  Count me in.

Feeling comfortable during intimacy is vital in any relationship. Being physically and mentally attracted to someone is a huge turn on. The more I know the person I’m hooking up with the more connected to them I feel. Hooking up means more when there are feelings involved. For me, sex is always better with someone I have an emotional and physical connection with.

4. Con: Things could get awkward.

However, sometimes if you’re too comfortable with someone, becoming sexual with them can get extremely awkward. News flash! Prepare to enter uncharted friendship territory. You’re going to see each other naked…or at least get all up in places you’ve never been before. It could get really weird.

If things don’t work out, it’s not only awkward for you but for your group of friends. Another thing to consider is the jealousy factor. If you do stay friends, how would it feel to bring future SO’s around each other? Will the green eyed monster come out, or do you roll with it? You may find that all communication becomes vague, or you stop talking altogether. I bet you’re regretting that first kiss now.

5. A Final Piece of Advice:

Tread lightly in the murky waters of casual hookups within your friend group. Then again, don’t even dip your toe in the water unless you’re 100% sure of what you want. If you’re on the same page or see a serious future with this person, I say go for it!

When all else fails, there’s always Tinder.