My Friend’s Ex is a Sugar Daddy, Should I Date him?

Chappelle

Hey Coach,

My friend was dating this guy for about 3 months. He paid all of her bills while they were dating and also fixed her car. Yeah, he’s a Sugar Daddy.

Long story short, they went on vacation together, she invited a few other friends (including me) and he paid for the entire trip.

While we were there nothing too obvious took place. He did try to flirt with me a few times, but I just figured he’s a big flirt anyways.

Once we got back to town though they got into a huge fight. She was very aggressive and they broke up. She gave me his number to call him because he had blocked her.

I called him, then gave her my phone so they could talk. He answered thinking it was me, then got upset and hung up. A couple days later he texted me just to say “hi”.


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Few days later he started flirting. Then he started flirting more. Then I started to flirt back. Finally he got to a point when he asked me to go out with him.

Now this is where I’m stuck. It’s been a few months since they broke up and she still talks about him. She’s still hurt.

She doesn’t know that we’ve been talking and texting and I feel awful. But I would like to go out with him to see where this goes…what should I do?!

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I appreciate you sharing your story. And this is a tough one. Generally speaking I’d steer clear from your friend’s ex…it’s bad mojo. 

The caveat here is if the person is really a friend (or family member). 

I’m bolding that word because it’s one of many words we use too loosely in western culture. 

Sidebar: what’s your personality type? Take my fun Personality Quiz to find out!

Is she truly a friend or is she just an acquaintance or someone you know via someone else? 

If she’s just an acquaintance the rules are different. 

Why you ask? Glad you did 🙂 


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Because, we can all play 6 degrees of separation (or Kevin Bacon :)) and find we know someone that we both have in common. 

Imagine always having to find the love of your life in another State/Country because you live in a small town and the people you are interested in have all dated someone you know! 

So yeah, the rules are different if it’s just an acquaintance. 

Not saying it’s a guaranteed yes!

But am saying it’s not as nerve-wrecking of a decision to make.

If this is really a friend, Sugar Daddy or not, it’s not something I’d advise.

Even if they only dated for a few months, you did mentioned she’s still hurt.

The reason I’d advise against it is simple.

It’s not worth the guaranteed bond of friendship, to possibly pursue someone that may be just a flash in a pan. 

Because if the relationship doesn’t work out, now you’ve also lost a friend in the process. 

I don’t want you to use your newfound powers for evil, but check out my post entitled “15 Ways to Capture his Heart: How to be the Woman he Can’t Resist

Not that you need to use these tips on a Sugar Daddy, but have fun reading it!

If you have a question you’d like me to answer here on “Dear Coach”, drop me an email!

-Coach Shawn


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