the playbook for pulling off the romantic equivalent of a Hail Mary pass-
turning your best friend into your boyfriend. Some say it can’t be done. Some say you’ll crash and burn. I say, if handled right, you have nothing to lose… not even the friendship. Flashback to high school. You met in study hall and bonded over failed science experiments and mystery meat lunches. You were friends until graduation. Maybe went to prom together, came close to kissing then decided you didn’t want things to get weird. Then it got weird. You each left for distant colleges- disappointed and relieved that nothing happened. So you cooled off the friendship but kept tabs on each other. Facebook, Twitter, Instagram… somehow you became the soundtrack to each other’s lives. How could you forget the person who surprised you with tickets to your favorite boy band reunion concert? That was forever. At least you thought so. And then, after college, when you returned home for holidays or jobs, you started hanging out again, this time meeting again in convenience stores, local book stores, coffee shops. Suddenly you were closer than ever with one itsy bitsy problem. Now you’ve noticed how handsome he is and want to be more than
friends. How to overcome history and start a new future? Here are some strategies to break out of the Friend Zone:
1. Shake things up. Catch him off guard with a compliment. You always think them, so why not say one? He needs to know that you see him as more than the boy who once evacuated the school after a Bunson burner incident.
2. Stop bringing up the past. It will only reinforce you as a friend. Instead focus on the future. Ask him what he’s doing over the weekend and make plans. Show him that you want to spend time with him.
3. Change the subject whenever he wants to talk about girl trouble. You aren’t his sounding board or his advice column. He needs to see you as girlfriend material… and no one thought Ann Landers was sexy. (Okay… maybe Mr.
4. Do things meant only for two. Having other friends around makes it super awkward to break out of the routine and get romantic. Try doing something you’ve never done alone. Hike a nature trail to a secluded spot, stop
at a local deli and bakery and have fun picking out items for a beach picnic, rent a tandem bike, go shopping for the perfect frame for your favorite picture of the two of you.
5. Touch. And not in some creepy, stalker way. But in a casual, ‘oops how did that happen?’ kind of way. Grab his hand during a scary movie, fly a kite and hold onto the reel together or fishing for that matter, dunk each
other in the pool or anything else that will get you two in physical contact. Maybe even offer to join him in washing his car then get into a sudsy sponge fight. The more that happens, that more comfortable you’ll feel when the hand
grab turns into a hand hold.
6. Romantic gestures. Bake his favorite cupcakes and put hearts on them when he’s down, bring him chicken soup when he has a cold, send him a ‘Thinking of You’ card when he least expects it, bring him a thermos of hot cocoa during a cold sports game . Men are all about action. So take some. But don’t paint him in a corner. He’ll only want
to escape and that will include your friendship.
7. Laugh. A lot. This is something you already do as friends so it should be easy. And this part of your relationship should never change. But if you bring a lot of friend drama to him, it might be time to dial it down and focus on having fun as a couple. The next time he invites you to hang out, bring a funny movie, a couple cans of silly string for a basement romp, or a box of water balloons on a hot summer day.
8. Get word to him through a friend. You can always deny, deny, deny, later. But in case he likes you- SCORE! Sure it’s juvenile, it’s high school, it’s whatever… but some of us aren’t good with the direct approach and it will give him time to think before feeling pressured into giving an answer. Another plus- he’ll see that your mutual friends support the status change- are even working to make it happen!
9. Write a note. Nothing long. Nothing over-the-top. Go for the three S’s- short, sweet and sincere. Something like: Zach,
you’re such a great friend and you’d be a great boyfriend too.
Will you go out with me? Text me Y or N. Either way. Nothing changes. xoxo
10. And if all else fails- hit the EJECT button on your expectations. But don’t ditch your friendship. You want him in your life even though it’s time to move on to greener pastures. Date someone else instead of mooning over him.
And who knows? The grass on your side of the fence might look greener to him too and he may decide to join you.