The Price of True Love

girl asking out a guy

Um, so, I just broke up with your best friend, but you wanna go out?

Dear ss,

Is it ok to ask a guy out after he has met my exboyfriend in the past? I have always liked this guy, and once I became single, I asked him out. He isn’t as wealthy as my ex,  however I’m looking for true love now. Please advise.


K. via email

Dear K.,

I don’t think there’s anything wrong with asking out someone who has met your ex in the past. Unless there’s more to the situation that just that. (Like, they met and are now besties and you stand to create a huge rift in their friendship. Not that I think you would do that.) If they are merely acquaintances, who cares?

Though I am wondering how long you dated your ex and how long you waited after you broke up to ask the new guy out. Are you hesitant because your break up is still fresh? I’m a big believer in downtime between relationships. Even if you’re not feeling hurt by the break up per se, I think it’s important to wipe the slate clean with some time alone to regroup.

I think it’s great that you asked him out, and I’m glad you’re overlooking financial status. You can’t put a price on love. (Yes. That’s right. I used a terrible cliche. But you can’t.) I have to ask though, were you not looking for true love before??

xo, ss


2 responses to “The Price of True Love

  1. Rachel,
    I love love love your book! Just bought it and I had to read the first 70 pages immediately.
    I couldn’t put it down. I could easily relate to your every story eventhough I’m a guy living in Las Vegas.
    (There seems to be few people of substance here so it makes dating very challenging and frustrating.)
    Reading your book made me feel like I’m the male version of you and your dating experiences.
    Any suggestions would be greatly appreciated.
    The best of success,
    M in LV

  2. Rachel Machacek

    Hi M in LV,

    Boy do I love hearing that you love (love love) my book. Made my week! And it’s interesting to hear the dating experience in so universal across city, state, gender.

    Every place has its frustrations, but every place has pros, too. You just have to find yours. I don’t believe in changing geography to date, but I do believe in making changes in your life to shake things up – maybe you just need to do something different. Take a new way to work, do things you like to do more often. Are you sure about so few people having substance or is it just the people you run into now doing what you do that aren’t good for you? Where do you meet people? What are you looking for? These are all things I consider when I check in with myself and take inventory of my own dating life.

    I want to hear more! Rachel

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