If you find that you’re interested in asking out your best friend, you’re not the first person to have ever experienced this.

Nonetheless, it can still be frustrating and intimidating to want to ask out your best friend and not know how or where to start.

Before you go gung-ho and start wooing your friend with wine and dinner, there are a few things you need to ask yourself first.

Dear Dan and Jennifer,

I like my best friend (there’s trouble there already) and I want to ask her out but I don’t know how. Many other guys like her too.

How do I make my self seem like the one she should go out with?  And how would I do that?

But please hurry! Were going to the movies tomorrow and I’m thinking of asking her out tomorrow.

- Kevin, Texas

Is there true chemistry there that goes above and beyond a friendship?

When you’re best friends with someone, there is a lot of chemistry there already. You both get along together great and you enjoy each other’s company. Basically, you can do anything and everything together. However, if you’re thinking about asking out your best friend, you need to really figure out if there’s more than just friendship there.

Do you feel a chemistry between you and your friend that goes above and beyond the friendship? Do you feel a sexual chemistry? If not, then you are probably better off staying friends. If you do, however, feel that there is something more between you and your friend, you have yet another question to ask yourself. Do you feel like your friend may return your feelings? This may not be something you get the answer to right away, but it’s important to consider before you ask them out.

Do you want to take the initiative and possibly get rejected?

Another thing to take into consideration is the fact that you might end up getting rejected and you might end up losing a friend too. If you suspect that this might be something that happens, consider leaving the friendship where it is at. If you simply can’t live with not telling your friend how you really feel, you need to realize that this may be something that changes the relationship forever, or possibly ends it. Make certain this is something you’re willing to risk before you take the plunge!

Avoid Getting Stuck In The Friend Zone

It generally is never a good idea to become friends with a person with the intent of becoming more than friends. Rarely does this work! Usually, you just get stuck in the friend zone. You end up being a great friend, one who they can share intimate talks with and confide in but realistically, you’re on the same level as their gay friends – someone who they care about deeply but would never consider a romantic relationship an option. If you like someone, be upfront and honest with them about your intentions rather than trying to sneak in the back door.

Telling Your Friend How You Feel

Okay, you’ve decided this is something you want to do and you’re willing to take the risk. Take your friend aside to somewhere you’re alone together and make sure there is plenty of time to tell them how you feel. Avoid cliché’s such as, “I’ve felt this way about you forever” or “I’ve always been in love with you.” These will most likely do little more than overwhelm and possibly frighten your friend!

Take it slow and be casual about it. Let them know that you’re interested in being more than friends and you’d like to spend more time together in a romantic way to see where it leads – and then leave it at that! Hopefully, a relaxed attitude will get you what you’re looking for and you never know – they could feel the same about you!