LILY Letter 103: How to Be More Than Friends

March 28, 2023

There are many important benefits to being bold and confident enough to be straightforward and say "I like you."

In order to BE more than friends means doing something to allow for that option.  The reason it is bold to confess your feelings is the risk that your friend may not feel the same way. And you never truly know until you ask.

In college, I had a female best friend for three years. I spent lots of time hanging out in her apartment, talking about life and relationships, while really avoiding both. She talked to me endlessly about the guy she wanted to date, while I was sitting right in front of her in her living room with nothing else to do. Of course I didn't muster up the courage to tell her how I felt until she was about to go on a mission--and I felt I had nothing left to lose. When I finally told her that I might like to be more than friends, she was uncomfortable and let me know that she was not interested in me that way. For the weeks until she left on her mission, our interactions were awkward.

The experience I have shared in this letter resulted from being young, bashful, and inexperienced. But I have observed many people in the mid-singles community making the same mistakes in their 30s, 40s and 50s. These are a few suggestions for managing the opposite sex "best friend" situation.

1. Don't use a friendship as a way to find love without risk.  If you genuinely have no interest beyond friendship, fine. Move forward with the friendship.  But don't do it secretly hoping for more and thinking you are laying a foundation for more. Being friends first is fine if there is acknowledged romantic potential.  But don't engage in what our friend Celeste Ulbricht calls "covert dating."  You may believe you can gradually get the other person to warm up to you and avoid the risk of being rejected outright. However, The rejection feels even worse after you have spent a long time as friends--something I learned the hard way from my college best friend.

2. If you like her, say it right up front. Rejection is not fun for anyone.  But it hurts less and wastes less time for both of you if you are honest about your intentions from the very beginning.

3.  Don't keep your foot in the door. If she tells you she only wants to be friends, believe her. Some men who really want more will accept friendship hoping that eventually they can change the other person's mind. This seldom succeeds and usually results in a big emotional investment by the person who really wants more.

If you have a best friend you would really like to date, wait no longer! Pluck up your courage and tell her how you feel. Take the chance! It may change your life.


Our featured podcast episode this week is Friends First? and our featured video is The Friendzone - Pro or Con? Our short this week is: Moving from Friendship to Love Affair. Here are convenient links to these FREE new resources. Enjoy!

LILY Pod: Friends First?

LILY Tube: The Friend Zone - Pro or Con?

LILY Short: Moving from Friendship to Love Affair

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