Risking A Friendship For A Relationship (Today Show)

Should you ever date your best friend? Why does my guy look at other women? What if he wants to take a break?

In this week’s segment I answer 3 more viewer questions on dating and relationships. Enjoy!

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From The Video

Laura asks:

I’ve had a guy best friend for more than 10 years. I got married in 2011 and divorced in 2013. Since my separation my best friend has been doing things he’s never done before (like buy me dinner, ask me about love…). Is it a good idea to turn your best friend into your soul mate, and if so, how do I go about telling him?

My Response:

There are three points to make here –

1. Best friends make great soul mates.

You’ve got a great foundation there.

2. How to tell him.

When it comes to telling him, you can say, “I feel more than just a friend to you right now. How do you feel?”

3. You don’t fear losing friendship, you fear rejection.

When anyone says, “I’m afraid of losing him as a friend”, I don’t buy it. This person doesn’t fear losing a friend, they fear rejection. It only changes the dynamic if you get awkward after the talk.

Elizabeth asks:

Why does my husband look at other women when he’s with me? I’m 12 years younger than him and I’m pretty attractive. What is he doing!?

My Response:

My question to you would be, well do you find other guys attractive?

Of course the answer is Yes, because no one ever finds nobody else attractive. You’ve set a rule that doesn’t allow him to win.

If it’s that he looks at other people in front of you, you need to set up a better rule for the relationship. ‘It’s not that you can’t find anyone else attractive, it’s that you’ve got to make me feel secure in this relationship.’

Courtney asks:

I’ve been in a 5 year relationship with a guy. He is 30 and I am 27. We’ve been living together for 3 years now, and even did a cross-country move together. Now he wants to “take a break” and live apart. It seems like he is terrified of commitment, but I am not sure how to move on. Do I continue to “date” and “see” this guy while living apart, or just cut it off completely?

My Response:

I’m going to assume that means a break from you, and not just from living together. With that, you have to change the way you’re looking at the situation. I always say, don’t value how much you like someone, value the investment they give you.

Many women make the mistake of saying, ‘I really like this guy, so I’m going to try really hard’. Instead of saying, ‘this guy is investing in me and giving to me, therefore I like him.’

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7 Replies to “Risking A Friendship For A Relationship (Today Show)”

  • Thanks for this. I could have really used this information a year ago when going through a situation similar to the first one with a friend. Hopefully it’s not too late to re establish our friendship.


  • Matt, if i want to ask you for advice on a man situation without doing it via public comments here or on facebook, is there a way? I do realise you are busy, but I am trying to turn a situation into a learning experience and could really use the perspective when you get a chance.

    Thanks, yet again, Matt!

  • What bitches! They cut you out at the best point! That’s a key thing to keep in mind, how much a man is investing in you

  • Exchange Theory. Hoda.. Kathy Lee… this is basic. Stop yourselves. Kathie Lee, Frank’s feelings matter too. Two snaps.

  • Nobody is saying you can’t be attracted to other people, but when you blatantly display that attraction in front of your partner, it’s incredibly disrespectful. I like your advice about setting better standards, but the question was never whether or not it’s okay to be attracted to other people.

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