Crossing the threshold from friends to lovers can either be highly rewarding or ruinous. Logically, you already have a number of important relationship elements taken care of, such as compatibility, trust and the ability to have fun. However, the decision to upgrade your friendship into a physical or long-term relationship can also be harmful to your friendship if he doesn't share your feelings or you break up in the end. By carefully gauging your compatibility with your friend in a cautious and sensitive manner, you can take the first steps to transforming your best friend into a life-long partner.
Step 1
Invite your "friend" on a dinner date at your place or a restaurant in town and ask him what his favorite parts about your friendship are. Create a mental list and add to it with your own observations, memories and feelings as you both mention the things you are most grateful for about each other's friendship. Make a promise between yourselves to maintain these things no matter what in order to preserve the qualities that you love most about your friendship.
Step 2
Test your compatibility by inviting him to events and outings that really resonate with your interest and gauge how engaged or bored he is during the event. Some good examples might include: a local arts festival, literary reading, concert, play, band, dance or anything else that interests you. While he may not completely share your passion about everything you enjoy, it may be a red flag if he falls asleep during your favorite movie.
Step 3
Work on knowing his friends. Hang out with him when his friends are around and see whether or not you fully like their company. While this may seem an obvious step, few things offer more insight into his personality than the people he chooses to spend time with (aside from you).
Step 4
Notice if he's as attracted to you as you are to him. While many guy friends will refrain from ogling their women friend's curves out of respect, few men can resist a skimpy, tight or revealing outfit that flatters your figure. Dress unabashedly sexy around him and notice if he sneaks a glance at you from time to time.
Step 5
Arrange a private retreat for a weekend wherein the two of you can get away from all work and social obligations. Choose a romantic destination such as a beach cabin or resort, or truly see each other's colors by taking a camping trip to the mountains. Allow your emotions to explore and observe how the chemistry between you two develops.
Step 6
Throw caution to the wind and kiss him. Notice how he reacts and act accordingly: blaming it on drunkenness or hormonal fluctuations if he doesn't seem interested--or in giving in to the romance if he does. Sometimes a male friend can be immune to suggestion and may need a blatant signal to get the hint.
Tips and Warnings
- Always make a point to protect the qualities that originally brought you two together as friends, and make sure he knows that you are always there for him to discuss his issues or problems as you did as a friend.
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