11 Questions To Ask The Side Chick Your Boyfriend Cheated On You With

A blog post about calling the side woman? Yes. Why? Because let’s face it, it happens and although I don’t always encourage this move sometimes the action has to be made, because if he’s cheating on you, he’s probably lying and not going to be 100% truthful when he gets caught out.

I’ve always said that if I ever got cheated on I wouldn’t want to find out through her (the side chick). I don’t want the other chick calling me, because in my mind she’s immediately the enemy, regardless of if she ‘comes to me as a woman’. I don’t want to hear it. In my opinion the chances of her calling my phone about fucking my man is because he refused to leave me and now everyone must suffer including my innocent self. You’ve caught me off guard and I probably haven’t prepared myself for this call. So please, chill.

What happens in the dark usually does come into light, so you will find out eventually.. and depending on how you feel and where the relationship is, this will allow you to decide whether or not you (the girlfriend, fiancée or wife) should call.

If you are going to contact her, here are a few important things to ask and remember okay? These questions depend on what your situation is and whether or not you’ll stay..

1) How long ago did you both meet?
This allows you to know exactly how long she may have been in the picture for, especially if he says different.

2) Did he ever share that he had a girlfriend?
Sometimes the other chick knows and sometimes, she doesn’t. Let her explain her side of the story..

3) Were you taken out on dates?
If he spent a lot of time with her, he probably spent money too, meaning this wasn’t just a fling. You get to understand how far he tried to play the both of you. Finding out about the dates helps you put two and two together. Those times he said he went out with his boys when he was probably laid up next to her. Or the time he spent half of Valentine’s Day with you because he said he had work, when he had planned a romantic evening with the other woman.

4) Did you have sex more than once?
Some men do mess up, but how often was he messing up? Ask!

5) Did you use protection?
Just like number 4 this is an awkward question, however the whole situation in itself is awkward. For your own sexual safety you need to know if he even bothered to wear a condom. Regardless of the answer make sure you go down to a sexual health clinic as soon as you find out your partner has been unfaithful.

6) How did things end?
She could have decided to end things so for this reason it’s important to ask. Your boyfriend might have carried on sneaking around if SHE didn’t terminate what they had going on.

7) Do you still have messages between the two of you?
You want that evidence because as Simply Oloni agony aunt Ebi and I agreed, seeing is believing and if you’re lucky, she might comply and show you messages, photos and voice notes of all the proof you need to see how low your man went to cheat on you. The evidence could include him speaking ill of you, acting like you’re an ex who won’t leave him alone or the mother of his child that refuses to get over him.

8) Do you love him?
This question might be tough, but listen, love doesn’t just fall out of the sky. Women do not wake up one day and decide that they want to be in love. He had to have played a part and done things for her to even get remotely close to the stage, so ask.

9) Are you still seeing him?
Your boyfriend might have told you that he stopped seeing her, but has he really? You better find out yourself..

10) Did you meet his family and friends/go to his house?
In this scenario she might not even be a side chick. I know it’s a tough pill to swallow, but if she’s meeting his family and friends and going to his house, you’re both clearly sharing him and he is now a two-timer. If the answer is yes, it will feel incredibly embarrassing, but it shows YOU the type of person he is, that is the important part with a lot of these questions.

11) How long was it going on for?
The length of it all matters. Was it a fling? A one night stand that he returned to repeatedly when convenient? How long was this emotional and physical connection for?

Remember this other woman is NOT your friend. I repeat this woman is not your friend, so once you’ve got what you wanted, keep it moving. The mistake I’ve witnessed a lot of women do, is befriend the other chick. In my opinion that is an extremely unhealthy relationship. You’ve created a friendship out of your dislike for a mutual person. What kind of bond is that? Do not meet up with her, stalk her, or stay with him because you’re afraid you’ll lose him, because guess what?… You already have.



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Dami Olonisakin

Dami Olonisakin

Editor-In-Chief and Founder of Simply Oloni.


  1. Roy
    September 27, 2016 at 12:16 am — Reply

    I just got into a relationship and I remember him telling me how his ex-girl friend cheated on him. now I saw a comment on her pictures on Instagram saying how much he loves her. I really don’t get. what can I do pls.

  2. Sila
    October 24, 2016 at 3:49 pm — Reply

    I became friends with the other women of my first real boyfriend, while they never had sex… they had sleep overs and shared cuddles and kisses. We were best friends for years…Even when he and I ended getting back together. We are not as close now but that was due to something totally diffrent.

    6 years later……Diffrent guy, My fiances ‘other women’ and I are friends. They no longer have an intimate relationship as of the first time she met me. She is great visits me when he goes out, we talk for hours, she also gave up his other secret women and does nicer things for me than my partner, we trust each other with bank details, money etc. ?. He’s currently away and we still speak everyday and catch up a couple of times a week. Honestly we could probably have a 3 way relationship without a problem. Apparent fiance and I speak about her and I think it does wierd him out that whenever he calls we were together or just on the phone to each other but he can just deal with it.

    I have always put it down too while I clearly have terrible taste in the type of guys I date, these guys obviously have incredible taste in the women they choose to be with ????

    Also Im clearly very strange after reading that….oh well so be it.

  3. December 14, 2016 at 4:45 pm — Reply

    Yeah I am all for talking to the babe not FIGHTING or INSULTING her.just asking questions after talking to your partner so you can get a better understanding of things,I saw some messages between my man and a girl and after I had a conversation with him I asked him to call her that I needed to talk to her,I asked a couple of questions,lol i spoke to her like I was talking to my younger sister and I moved on from it

  4. Marie
    September 11, 2017 at 4:09 pm — Reply

    I want to message her and ask questions so bad bc I feel like she would tell me more, I’m just worried she will go straight to him and tell him that I’ve messaged her. What do I do?

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