Guy friend asking a "hypothetical what if" about dating?

[Anonymous]

I have a boyfriend and love him lots. But my brother and my boyfriend pointed out that I've been calling my guy friend Simon too often. Which I suppose makes sense, so I've been reflecting on it. Simon and I have known each other for 6 years. He regularly video calls me around midnight or later (which I'm OK with since I have insomnia). We just study, sometimes chat, usually silent over call.

As you see in the text, he admits he was flirting. And then later, denies that he ever flirted with me...

Somewhere along the way, he dropped a "you're attractive, you have your own personality". But I assume it wasn't genuine, since he seemed to be comforting me when I mentioned feeling insecure.

After some more talking, I told him I had to go. It was late, I had to sleep. Then he threw such a curveball question at me. It shocked me a lot. I don't understand why he would ask that. I know Simon mentioned this other girl and how he watches himself around her.

Overall, it was worrying because I crashed over at their apartment (a bunch of old classmates). Despite never talking to Simon or me gossiping about our past, my girl friend Anna made a side comment about him. After a few days of partying and sleeping, Anna said "I hope you don't mind me asking but... Simon seems to care about you a lot. He kept turning back to ask about you. Is there history?"

I guess... Simon decided to deny flirting (even though he said he did) because he remembered I've been with my boyfriend for a few years. But I'm not really sure what to do for the friendship besides pretending nothing's wrong? Overall I just hope this was a fun story and read for someone on this forum haha

Updates

+1 y

* side note: when I mentioned the flirting, it was a few years back before I started dating my boyfriend. Simon doesn't flirt anymore. But that's why I mentioned that my friend noticed he seems to still care about me a lot.

I did tell Simon that we need more boundaries and to keep it PC between us.

[SueShe]

One does not "just flirt" without a very good reason. The definition of the word "flirting" is:

"a sexual behavior involving spoken or written communication, as well as body language, by one person to another, to suggest interest in a deeper relationship with the other person".

Now, we all know what a deeper relationship is meant, right?

I would be very careful and stop this flirting and making sure he understands that you will tolerate n flirting while you are in a relationship.

Unless of course, you are n longer interested in your boyfriend and that you need someone new to replace him. But then, have the decency to tell your boyfriend that you found someone new to replace him.

All you will succeed by allowing Simon to flirt with you is to create jealousies. Is that really what you want?

[Asker]

Hi SueShe! Thanks for the advice. To clarify, the flirting happened 3 years ago. I just meant that his texts (from now) are reminding of his actions from before. We have not been flirting at all.

I love my boyfriend a lot, so I'm trying to figure out how to still be friends. -- Without destroying a 6 year friendship. But my boyfriend notices because when I sleep over, Simon would call me at 1 AM. I really did not mean to hurt anyone or to create jealousy. 😕

[SueShe]

You have to make it clear to your boyfriend that the past is behind you and that only he counts in your life.

You should probably also tell Simon to refrain from calling so late because you don't want to cause any problems with your boyfriend. You can tell him without risking to lose his friendship that you don't mind if he calls shortly let's say before 10 pm and that your boyfriend is aware of you calling. If you hint that your boyfriend is aware, it may lead him to call at more civil times and to perhaps refrain the number of calls to a minimum.

[molonski2]

He is just seeing where he stands this kind of thing happens all the time , in hindsight , things always change.

[boobliker]

If you want to keep the friend do not fuck him in any way.

[Avicenna]

just don't be alone with him