I flirted with my best friend's boyfriend to test his loyalty and now she's upset.

[MaximumGear]

My best friend "Sara" (27F) and I (30F) have been very good friends for almost 3 years. I absolutely love her to death, so none of my actions are motivated by jealousy or hatred, before anyone accuses me of such.

When we first met, Sara had never been in a relationship before and was still sexually inexperienced at the time too. I had the opposite relationship experience, so I often would help Sara through the world of dating and give her advice.

One thing I distinctly remember her requesting years ago was that she wanted me to flirt with her future partner and see how he would react. And if he came onto me, to let her know so she could know how trustworthy he is.

Sara had one short relationship with someone (one who I did not "test"), before meeting her current partner. She really loves him, which is great to see her so happy, but I have always had my doubts about him from the beginning. He checks all the boxes and seems great on paper, but my experience and intuition tells me he seems like the type to cheat. Or, that maybe he's more of the poly type and could be hiding it from Sara. It didn't help that Sara told me one day that---after they talked about their past romantic experience with each other--- he revealed he had his share of hookups and ONS. Sara thinks he has slept with 30+ women at least., compared to this being Sara's second relationship and first ever sexual relationship.

So I took on Sara's test request and flirted with him. The first time was when we were at a party (Sara was also there, but there was a moment when we two were alone), and the other time was at another event when I flirted and offered my phone number for an "innocent" reason, but would still be inappropriate if he took it. He did take my number, and honestly, he straddled the line between being receptive but clearly holding himself back, which is good he didn't fully flirt back, but it still concerned me he had to restrain himself in the first place.

The other day, I got a text then phone call from Sara accusing me of trying to get with her boyfriend and that I betrayed her. (He had told Sara that I was coming on to him, which is a good sign he told, the very thing Sara wanted to check.) I reminded Sara of what she said years ago, and she said she was joking back then (though she definitely wasn't) and that it was years ago and I should have asked.

I NEVER HAVE AND DO NOT WANT SARA'S BOYFRIEND. Never. But I can't help but feeling like I'm taking crazy pills when Sara wanted me to do this then said she didn't.

[Jaunty]

Sara needs better friends.  A true friend would not have inserted themselves in her relationship because it's wrong and destructive.

If she wants her friends to do this then she is not in any place emotionally to be attempting a relationship.  

Why would you?

[Seraphim]

So guys set out to trap him and it blew up in your faces . Consequences of playing games. 

[kctiger]

This is unreal. There is so much immaturity in this story, I don't know where to begin. I thought this was about some highschool kids, but nope, you're all at or near 30. The boyfriend got entrapped by his girlfriend's best friend at the request of his girlfriend. Sounds like a movie plot. She isn't ready for a relationship with him or YOU, for that matter. The boundaries were crossed all around. I can't imagine having a friend ask me to hit on his girlfriend. That's now how things are supposed to work. I certainly wouldn't have friends that expected me to do something like that either. 

[Wiseman2]

14 minutes ago, MaximumGear said:

I often would help Sara through the world of dating and give her advice.

I took on Sara's test request and flirted with him. The first time was when we were at a party. I flirted and offered my phone number for an "innocent" reason, but would still be inappropriate if he took it. 

 I got a text then phone call from Sara accusing me of trying to get with her boyfriend and that I betrayed her. 

Unfortunately it's a horrible "test". You basically set him up and tried to entrap him. He did not flirt with you. You forced this and he was right to tell her you did this. Don't give people any more dating advice. Stay out of other people's relationships.

[Kwothe28]

So he didnt take the bait and she tried to save her face in front of him by being mad at you?

Yeah, that guy is way above both of you in maturity.

[bluecastle]

13 minutes ago, kctiger said:

There is so much immaturity in this story, I don't know where to begin.

This sums up my reaction as well. Were the story not so fleshed out I'd be tempted to assume the post is a prank in the manner of the one described. 

Anyhow, I'd say this is a very good moment to look in the mirror and humbly decide who you want to be, as an adult. Is the answer someone in her 30s guided by the logic of middle school? Or someone who learned, through a set of unfortunate choices, that such logic has no place in adulthood or adult lives, save those whose highest aspiration is realty TV stardom? 

Among the many concerning facets of this is your unflappable belief that an absurd, offhand remark made years ago was not a joke, even when the person who said it tells you that's exactly what it was. In addition to highlighting how little you think of your friend's ability to handle herself in the world, it speaks to a very deep impulse to rationalize and justify behavior below the norms of many elementary school students.

I mean, c'mon now. If I friend said something like "If I ever date another loser again please just kill me" would you follow up years later?   

 

[MaximumGear]

Yes, I can see now it was not the right choice to make and I definitely apologized to her the last time we spoke. But I have to say I disagree that such a test is always a bad idea. I could have asked Sara again if she was sure (though what she said three years ago was not an offhand comment and she was serious), but having outside people put prospective partners can give you a more accurate picture of your partner before you get hurt, or worst yet, waste years until getting hurt. But that's just my two cents. I do regret how it played out with "Sara" though.

[Jaunty]

3 minutes ago, MaximumGear said:

But I have to say I disagree that such a test is always a bad idea. 

If you're 12.  By the time you're close to 13 and beyond ... yeah.  Bad idea.  Always.

[Wiseman2]

5 minutes ago, MaximumGear said:

 I have to say I disagree that such a test is always a bad idea. 

To be honest the test in itself would be a reason for me to dump someone immediately. That type of manipulative, grossly jealous and immature craptest has no place in decent men's lives.  Even after it backfired you think stunts like this are a good idea?🤯

[bluecastle]

7 minutes ago, MaximumGear said:

But I have to say I disagree that such a test is always a bad idea.

Not to pile it on, but I really hope that, sooner than later, you come to look back at writing a sentence like this as time you grew out of, rather than further into. 

Sure, generally speaking, we introduce prospective partners to friends to get their take. That is very—very—different from concocting completely dishonest tests in order to gauge...honesty.

If someone's view of the opposite sex is so low, and if someone is so deathly afraid of being hurt emotionally that they'd engage in something like this, the solution is very simple: do not date until you are ready for, and open to, all it can entail, including the potential for some pain and heartache.

That's the advice I'd give any friend who was as preemtively hung up on the pitfalls as you are. Interestingly, Sara didn't seem to be asking for any advice on that matter, so maybe explore what anointing yourself as her dating parent offered you. It seems you feel that you are the more experienced and mature one, but everything about this story points to that not being the case. 

[Lambert]

37 minutes ago, MaximumGear said:

but having outside people put prospective partners can give you a more accurate picture of your partner before you get hurt, or worst yet, waste years until getting hurt. But that's just my two cents

This is not healthy logic. 

If you're in a relationship and a test is needed, save yourself the trouble and embarrassment and just end it. 

Stay out of your friends' relationships. Friends don't let friends drive drunk. Everything else is none of your business. 

[gamon]

2 hours ago, MaximumGear said:

 I can't help but feeling like I'm taking crazy pills 

Understandable.

[moodindigo91]

2 hours ago, MaximumGear said:

My best friend "Sara" (27F) and I (30F)

To pile on, this is extremely immature. You are also older than your friend, and apparently more "experienced". You should have known that this was the wrong decision. This is not a sitcom. Flirting with your best friend's boyfriend is not likely to have positive outcomes. I'd say, if you were going to do it, you should have at least spoken to her about it JUST prior to taking action. Instead, you took action based on some conversation you had when you first met, which according to you, was probably around 3 years ago. And of course, for extra context, please consider everything that's happened just in the world in the last 3 years, a global pandemic being one of them. Also given the fact that she dated someone else before her current partner who was not subjected to the test, I think she wasn't expecting this in any way. She probably didn't even recall this conversation until you flirted with her boyfriend. 

I think she's rightfully upset. Although it's too late now, this action shouldn't have been taken without a direct request from Sara to do so with her current partner specifically. 

Anyway, the test IS always a bad idea, especially since the man's action in response can mean anything and can have completely innocent reasons behind it. He took your number, for instance, probably didn't want to, but did so in order to not upset you, the best friend of his newish girlfriend, and cause friction with him and his girlfriend. Something you might take as deceptive behavior could have completely innocent reasoning. Also, a "test" may also be passed with flying colors by the most abusive or worst partner imaginable. You are not even sure what you're testing. And if one thing is for certain, "loyalty" can't be tested by anything but time. It's always a bad idea. I wouldn't do it again with anyone's relationship. 

[Batya33]

2 hours ago, MaximumGear said:

 But I have to say I disagree that such a test is always a bad idea. I could have asked Sara again if she was sure (though what she said three years ago was not an offhand comment and she was serious), but having outside people put prospective partners can give you a more accurate picture of your partner before you get hurt, or worst yet, waste years until getting hurt.

It's simple -if you feel the need to test you have your answer -you're in the wrong relationship. Without trust there is no relationship. IMO given your attitude and behavior you fail the test of loyal, thoughtful, good friend in this situation.

[Tinydance]

54 minutes ago, gamon said:

Understandable.

I hope the pills can help the crazy go away 😜

[Tinydance]

2 hours ago, MaximumGear said:

Yes, I can see now it was not the right choice to make and I definitely apologized to her the last time we spoke. But I have to say I disagree that such a test is always a bad idea. I could have asked Sara again if she was sure (though what she said three years ago was not an offhand comment and she was serious), but having outside people put prospective partners can give you a more accurate picture of your partner before you get hurt, or worst yet, waste years until getting hurt. But that's just my two cents. I do regret how it played out with "Sara" though.

Are you actually being serious? I mean, you are 30 years old. What you did sounds like something out of 90's/early 2000's teenage movies like Mean Girls, Ten Things I Hate About You, etc.

There isn't really a need to "test" anyone's boyfriend. If there is any evidence the boyfriend is cheating then Sara needs to confront him, as it's between the two of them. However there actually was no evidence he was cheating or doing anything wrong.

You seem to have made some judgements about him based on the fact that maybe he's dated and slept with a fair few women. How do you actually know he slept with 30 + women? Did he tell Sara this and then she told you? Or you were just guessing? If you were just guessing, that makes it even worse.

Just because your friend had no dating or sexual experience before her boyfriend, but he did, doesn't mean he's a bad guy or wrong for her. Also if he's in his late 20's or his 30's it's not necessarily a super huge number if he's been with 30 women. Maybe he was actually dating at least some of those women.

Also maybe yeah he hooked up with some women when he was single. But that doesn't automatically mean that when he's actually in a relationship that he would cheat. If he's single he actually can do what he wants.

I think the bottom line is Sara actually didn't ask you to do this. You said she's happy with him. If she's happy then what was the need to get involved in their relationship? Can't you just be happy for your friend that at 27 she actually found her first relationship?

You shouldn't get involved in other people's relationships. Unless maybe your friend's partner abuses them or you actually found solid proof that they're cheating. You should just mind your own life. Especially as you are in your 30's.

 

 

[catfeeder]

What, exactly, is your question to us?

How can we help you?

[Cherylyn]

Just apologize.  Tell Sara that you were trying to help her by testing her boyfriend because she requested this test.  Tell her that you were not interested in her boyfriend and had her best interests at heart.  Then tell her that from now on, she is completely responsible for her relationships whether they're successful or not.  Vow to stay in your own lane, mind your business and you're available for moral support, however not any form of aid.  Enforce healthy boundaries with Sara.  Lesson learned.  Never meddle.  Know your place.  Bite your tongue and look the other way. 

[Tinydance]

Also I don't think there is a need to give outside perspective on your friend's partner. Unless they're actually a bad person and did something wrong, I don't think it matters what you think of them. We don't always click with or like everyone but the main thing is our friend likes their partner. Even if we don't like them (unless for good reasons) then we just need to be nice and get along. Our friend has chosen this person and we should respect that.

[lostandhurt]

This wasn't a test, it was a statement to her bf. "I don't trust you"

It is that simple.

Lost

[MissCanuck]

Sara sees right through through your BS. 

This was you trying to get with her boyfriend. Plain and simple. Now you're back-pedalling and trying to pretend it was a "test" because he didn't want you. 

Leave Sara and her boyfriend alone. And work on your boundaries and maturity. Don't go after friends' boyfriends. 

[Carnatic]

I don't know why you wouldn't tell Sara about your plan beforehand if it was something you were doing to help her.

Maybe it was meant as a joke, or maybe she forgot she said it. It was 2 boyfriends ago and said at a time when she'd never been in a relationship before. I don't know what part of it you interpreted as a request to just surprise her with 'hey I flirted with your boyfriend and here's how he reacted'.

[JoyfulCompany]

14 hours ago, MaximumGear said:

So I took on Sara's test request and flirted with him

Uhm... "test request"?
1. It's just something she've said 3 years ago. She may or may not have meant it at the time as a potential thing to do. She never asked you to specifically do it now with this man.
2. Even if she asked you to do it two weeks ago, you don't have to agree to such ridiculous scenarios. As a side effect it could have devastating consequences for a friendship. If the man flirts back - Sara may built resentment towards you. If he doesn't flirt back - now her boyfriend will dislike you and if they get serious, Sara may distance herself from you. But in all cases - it brings unnecessary havoc in the relationships between all people involved.

I understand that you care about Sara but you've manifested it in the worst way possible by: a. not consulting with her and b. internally accepting the role of an "interfering patron", somewhat looking down on her for having less relationship experience.

Hope you're able to patch your friendship up, but, please, never meddle like this again.

[Jaunty]

I'd hate to imagine some of the things I may have thought were a good idea three years ago ...