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My Sister Wants To Date My Ex

"Ask April" Author of the best selling "Date Out Of Your League" at

Why Do I Feel So Weird About It?

Dear April,
My sister asked me if I would mind if she went out on a date with my old boyfriend. I said it was fine, but now I don’t feel fine. What’s wrong with me?
Sister Act


Dear Sister Act:

Nothing is wrong with you – except for the fact that you lied to yourself and your sister, and that’s why you feel like something is wrong. But don’t worry. We can fix that. Here’s the problem.

Ex Doesn't Mean Dead

You broke up with your boyfriend, but you still have feelings about him and your relationship with him. It doesn’t mean you still love him. It doesn’t even mean you still like him.

You may have moved on in many ways. In fact, you may even be in a great new relationship where everything is going well and you never even think about your ex, normally. But when your sister brought him up as a possible date for her, she brought him back onto your “radar screen” and now you’re wondering if he was always interested in your sister when he was dating you and if so how much.

You’re probably wondering what kind of communication your sister and your ex had while you were dating, while you broke up, and since then. For example, when he came to pick you up when you were dating, and you weren't ready, and your sister was chatting with him until you came downstairs, what was really going on?

You’re also probably wondering about all the reasons you broke up with him, or he broke up with you – even if you’re happy in your relationship now. In fact, you may have some new anxiety about what's going on in your current relationship, and if anyone like your sister, is interested in your current partner -- and you don't know about it.

Don't Freak Out

Relax. This is all normal. Any time someone from your past is brought into your present – in a fleeting mention in a conversation, in a dream, or in a real life situation where your sister wants to date that someone, you have these thoughts and wonders. So allow yourself to ask all those questions of yourself without feeling abnormal worry or guilt.

Seduced By Good Manners

The next thing you have to understand is that you allowed yourself to be seduced by your sister’s civility. Her good manners and her doing the right thing by asking your permission, in a sense, to date your ex, was very gracious. She didn’t have to do it. She could have just gone out and dated him without telling you, letting you find out from someone else, or telling you down the road sometime. But she didn’t. And because she was so civil, you felt that you had to be just as civil, back to her – but you mistook civility with actions.

Many people do this – mostly women with self-esteem that needs a little amp-ing up. When someone is gracious to them, they feel that they have to give them what they want. But what is more important is doing what you mean to do – not what the other person wants you to do. Don't just respond to what it is they're saying. Respond to what it is they're asking for or telling you.

Rights vs. Right

Now you have to get to the core of the problem. You’re feeling funny because you really don’t want her to date your ex boyfriend, and you don’t really have any right to tell her not to. You’re afraid that you’re going to create a confrontation by telling her your true feelings – that you don’t want her to date him -- and you’re trying to avoid that by saying yes, she can date him – when you really want to say no, she can’t.

But you also know that even if you tell her she can’t date him, you don’t own him – and he may even very much want to date her. So you say yes to save face, so that you won’t have to be seen in a defeat situation – by telling her she can’t date him and then watching while she does anyway!

Women have a built in biological mechanism that keeps us from fighting because we are not as physically strong as men, historically, and we would be wiped out if we fought them. That mechanism creates a "fight or flight" syndrome. Adrenaline is released into our body when we feel a confrontation coming on. The adrenaline causes anxiety.

That is what you are feeling.

There is a way to reduce this discomfort, and that is by knowing what is happening to you and why it is happening to you. That alone will alleviate some of your discomfort.

Tell Her You Don't Want Her To Date Him

What you have to do now is tell your sister that you were really taken aback by her request. You’re very appreciative that she came to you first to ask your permission when she didn’t have to, and you’d love to know more about the relationship. Ask her what you want to know.

Have a cup of coffee and find out all those questions that are nagging at you. Tell her how you feel – that you’re embarrassed and shocked that you have these feelings about the fact that she is interested in him – and him in her. But you have them, nonetheless.

Tell her that you’re not sure how you feel about it, and you’re going to have to take a little time to get used to it.

Then comes the hard part. The truth.

Tell her that you really don’t want her to go out with him. Tell her that it makes you uncomfortable. Tell her your true feelings about him – that you don’t have any romantic designs on him, but it still makes you feel uncomfortable, nonetheless.

And tell her that you realize it’s really not your choice to make, and that if she does decide to go out with him, you’ll find a way to be okay with it -- and that you’re open to any of her suggestions on ways to make this go more smoothly.

Let Go And Move On

Then comes the really hard part. You have to do what you said you’re going to do! That’s why it’s important to tell the truth – to your own self and to others.

Lies complicate things and this situation is already inherently complicated. If you lie about any part of this, you will find yourself in a big mess that will be difficult to unravel. If you are honest that you don’t like this, but you’re going to try and be okay with it, you don’t have to hide your feelings so much.

If you choose to not be around when they are, your sister will at least know why. And the other par of all this is that you don't have to like this, and you don't have to pretend to like it. You didn’t do anything wrong if you were honest.

Sincerely, April

Ready for even more bold, brutally honest, and always helpful dating advice? Visit Web site, There, you'll find informative articles, expert columnists, interactive quizzes, and free giveaways! And don't forget to also check out my workshops, designed to help you find you real "soul mate"!

© April Masini. Making it happen for you!
If you’re ready to get serious about finding a relationship that will really work for you—but aren’t quite ready to sign up for an arranged marriage—then my workshops on dating, love, and all around success might be just what the doctor ordered. Please visit

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