How to Date a Best Friend's Older Brother

There's that one guy that you've had a crush on for years. The crush seems to have started when you were just a tween. Now that you're all grown up you want to work on improving that relationship. Follow these steps to date a best friend's older brother.

Instructions

Difficulty: Moderately Easy

1. Feel the friend's older brother out to see if there's the chance of a romantic relationship. Try simple flirting when you visit your best friend. Make it a point to include the older brother in a conversation or two.
2. Mention to your best friend that you enjoy her older brother's conversations and sense of humor. Ask if his girlfriend also enjoys his humor. This will give your best friend a chance to spill the beans about his dating life, or lack thereof.
3. Gather all the information you can about your best friend's older brother. Ask what he does in his spare time. You may find that he frequents certain places on a regular basis.
4. Acknowledge your best friend's older brother if you see him out in public. This will remind him that you exist.
5. Talk to your best friend about your interest in dating her older brother. Do not try to sneak behind her back and date him because that will only hurt her feelings when she finds out. If she thinks it is a great idea, she may be able to help set you two up on an actual date.
6. Ask your best friend's older brother out for a casual cup of coffee or a drink. This will start the dating game for the two of you.