u/Kittykat2108

Hi everyone, I (25F) need some outside perspective because I’m not sure if I’m overthinking this or if something is actually off.

I’ve been dating my boyfriend (30M) for about 5 months. So far, things have felt really good between us. We seem aligned on values, long-term goals, and what we want in life (serious relationship, stability, building something together, etc.). I also generally feel secure in how he treats me and how he talks about me.

The issue is more about one of his close friends/business partners.

This friend is someone my boyfriend reconnected with recently after not being in touch for years. They now run a business together. From what I’ve heard, this friend has a bit of a history of being a “womanizer,” though he’s been in a long-term relationship (around 8 years) now.

I’ve met him a few times in group settings, and I’ve always felt a bit uneasy around him, even before anything specific happened.

Here are some examples of behavior/comments that stood out:

• He often makes comments about women’s appearances (like he prefers blondes to brunettes and his gf is a brunette), even in front of people, including his girlfriend.
• My boyfriend and another friend set a “boundary” with him saying they would cut him off (socially and business-wise) if he ever cheated on his girlfriend since she is a sweetheart and they wouldn't trust him after that.
• The last time we all hung out (I was the only woman there), he made a comment suggesting that stress could be solved with sex when talking about my boyfriend being stressed?? I was very uncomfortable. My bf didn't say anything. I just assumed it was normal talk?
• He also asked the group this question: “If you cheated on your partner, would you want them to know or not?” and then said he personally wouldn’t want to know and wouldn’t tell his partner either if he cheated, which felt… off. It made me believe he cheated on her already and was testing territory.
• On social media, he also follows a lot of very specific types of women and makes general comments that feel a bit inappropriate given he’s in a long-term relationship.

Recently, I posted something on Instagram about a “woman’s daily routine” post that didn’t include any mention of a partner, and he replied with “what about sex?” which again felt a bit strange to me.

For context: I’ve never liked this guy much since I met him. It’s just a gut feeling + some of these comments that feel uncomfortable.

My boyfriend, on the other hand, does not behave like this. He’s been respectful, affectionate, and has never given me reasons to doubt him. He also doesn’t agree with a lot of what his friend says and has even challenged him before.

I have, however caught him in a couple of lies. He doesn't like to post on social media and I've read way too much into it. One of his female friends recently published a book and was doing a giveaway and he tagged my friend in the comments and nobody else. Then my friend tagged me and I noticed he didn't tag me. I initially read too much into it, or so I thought. I stuck with the idea that he was trying to hide me on his social media even though I've never tagged him on anything or acted like I wanted to be posted on everything. His excuse for not tagging me was that this friend of his had already prepared a book for me signed and all. When I met her, she showed up with only one book (his) but not "mine".

He does have female friends (since elementary school); they sometimes hang out for beer but it's nothing serious. I also have a bad feeling about them. Something is off about them specifically.

Still, I’ve been seeing a lot online (TikTok/Instagram) about how “if his friends are disrespectful or flirt with you, he is cheating on you,” or that friends “know what he’s really like.” That’s what’s making me spiral a bit and question things.

So:

• Is this just a case of a questionable friend with bad boundaries?
• Should I be reading anything into this about my boyfriend, or is that unfair?
• If this friend ever tried to flirt with me, what would that realistically indicate (about him vs. about my relationship)?

Hi everyone, I (25F) need some outside perspective because I’m not sure if I’m overthinking this or if something is actually off.

I’ve been dating my boyfriend (30M) for about 5 months. So far, things have felt really good between us. We seem aligned on values, long-term goals, and what we want in life (serious relationship, stability, building something together, etc.). I also generally feel secure in how he treats me and how he talks about me.

The issue is more about one of his close friends/business partners.

This friend is someone my boyfriend reconnected with recently after not being in touch for years. They now run a business together. From what I’ve heard, this friend has a bit of a history of being a “womanizer,” though he’s been in a long-term relationship (around 8 years) now.

I’ve met him a few times in group settings, and I’ve always felt a bit uneasy around him, even before anything specific happened.

Here are some examples of behavior/comments that stood out:

• He often makes comments about women’s appearances (like he prefers blondes to brunettes and his gf is a brunette), even in front of people, including his girlfriend.
• My boyfriend and another friend set a “boundary” with him saying they would cut him off (socially and business-wise) if he ever cheated on his girlfriend since she is a sweetheart and they wouldn't trust him after that.
• The last time we all hung out (I was the only woman there), he made a comment suggesting that stress could be solved with sex when talking about my boyfriend being stressed?? I was very uncomfortable. My bf didn't say anything. I just assumed it was normal talk?
• He also asked the group this question: “If you cheated on your partner, would you want them to know or not?” and then said he personally wouldn’t want to know and wouldn’t tell his partner either if he cheated, which felt… off. It made me believe he cheated on her already and was testing territory.
• On social media, he also follows a lot of very specific types of women and makes general comments that feel a bit inappropriate given he’s in a long-term relationship.

Recently, I posted something on Instagram about a “woman’s daily routine” post that didn’t include any mention of a partner, and he replied with “what about sex?” which again felt a bit strange to me.

For context: I’ve never liked this guy much since I met him. It’s just a gut feeling + some of these comments that feel uncomfortable.

My boyfriend, on the other hand, does not behave like this. He’s been respectful, affectionate, and has never given me reasons to doubt him. He also doesn’t agree with a lot of what his friend says and has even challenged him before.

I have, however caught him in a couple of lies. He doesn't like to post on social media and I've read way too much into it. One of his female friends recently published a book and was doing a giveaway and he tagged my friend in the comments and nobody else. Then my friend tagged me and I noticed he didn't tag me. I initially read too much into it, or so I thought. I stuck with the idea that he was trying to hide me on his social media even though I've never tagged him on anything or acted like I wanted to be posted on everything. His excuse for not tagging me was that this friend of his had already prepared a book for me signed and all. When I met her, she showed up with only one book (his) but not "mine".

He does have female friends (since elementary school); they sometimes hang out for beer but it's nothing serious. I also have a bad feeling about them. Something is off about them specifically.

Still, I’ve been seeing a lot online (TikTok/Instagram) about how “if his friends are disrespectful or flirt with you, he is cheating on you,” or that friends “know what he’s really like.” That’s what’s making me spiral a bit and question things.

So:

• Is this just a case of a questionable friend with bad boundaries?
• Should I be reading anything into this about my boyfriend, or is that unfair?
• If this friend ever tried to flirt with me, what would that realistically indicate (about him vs. about my relationship)?

Thanks in advance for any perspective.