[youngbuck01]

I’m a 25 years old guy and moved to a new apartment complex about a year ago. I met this other guy that lives in the complex, he’s 22. So we started hanging out here and there (he’s a little bit mentally slow, but still cool to hang with). Then he invited me to play cards at his place one time. This is when I met his mom. She’s in her late 40s and I would say that she’s fairly attractive. She’s separated from her husband and my friend stays with her often but lives with his father the next town over. So over the past 8 months or so that I’ve know them, I’ve hung out at my friends mom’s place multiple times. While hanging out these are some of the things his mom has said or done:
she has “joked” about her and I taking a bath together (she was laughing a lot when she said this to me), she routinely leans into my shoulder/back ( I can feel her breasts pressed against me when she does this), she tries to “spank” my bottom saying I’m being “fresh” when I’m horsing around with my friend, a couple of times – has shown me a new bra that she bought ( not while she’s wearing it though) to see what I thought, once told me she “didn’t care if I saw her naked”, told me she was going to sleep over at my place ( she was laughing a lot when she said this to me), and was very excited to show me how she looked in her swimsuit ( she, my friend, and I had planned to go to the beach, so I met them at her place, this is when she presented herself to me after putting on her swimsuit). These are just some of the flirty things she has done/said to me during the time I’ve known her. I would have physical relations with her if it did get to that point but I don’t know if I should because of my friend. He doesn’t seem to notice/care about all the flirting his mom has done with me… What should I do?

[AskApril Masini]

If you want to date your friend’s mom, you should probably discuss it with him first. There’s a code among guys and dating a friend’s mother definitely falls within it. Tell him you think his mom is really great, and you think she likes you, and you’re interested in dating her, but only if he’s okay with it.

[youngbuck01]

Hi April,

Thank you for the advice. If I do decide to go ahead with any sort of relationship with my friend’s mother, I know that I at least owe it to my friend to pass it by him first so that I am not doing something behind his back that he may not be OK with. I do have a feeling though, that if I do tell him that I am interested in seeing his mother that he would not be too pleased with that proposal. I think I’ll drop some hints about the possibility of my having a relationship with his mother and see how he reacts, then I’ll know better how to proceed.

Thank you again,
Youngbuck01

[AskApril Masini]

Don’t “drop hints”. Be clear and let there be no misunderstanding what your intentions are — to date his mom. It’s understandable that he won’t be happy about this, but if you’re okay with his being unhappy, then you can at least know you didn’t go behind his back and lie to him. Age is one thing, but having the character and maturity to be up front closes any age gap. 😉

[youngbuck01]

Hi April,

Ok, I will “man up” and do the right thing and be straightforward with my friend regarding how I feel about his mom (ie. that I’m attracted to her) and also relay the fact that she has been flirting with me for awhile now. And I’ll see how he reacts to this and proceed from there….

[AskApril Masini]

Tell him you want to take his mom out on a date. The last thing your friend wants to hear is that you’re only interested in sex. Any adult child wants to know that their mother isn’t being taken advantage of. He’s going to want to hear that your intentions are good. I think that knowing that, you can take it from here.

[Ethan Morales]

It’s clear that the mother’s behavior is very flirtatious and sexual in nature, and you’re understandably attracted to her. However, there’s a strong ethical and relational layer here because she’s your friend’s mother. Even though your friend may seem indifferent, acting on these impulses without considering him could cause serious harm to your friendship.

April’s advice about transparency with your friend is key. While it may be uncomfortable, being upfront and honest shows maturity and integrity. By telling your friend that you’re interested in dating his mom, and that she has been showing interest in you, you remove ambiguity and avoid acting behind his back. This approach preserves your character, even if it risks temporary tension in the friendship.

The emphasis on dating rather than casual sexual relations is very important. Your friend will likely be more concerned about his mom being treated respectfully than about age differences or flirtation. Framing your intentions as serious and considerate shows responsibility and reduces the likelihood that your actions will be seen as exploitative or selfish.

You should also consider the mother’s perspective. While she’s clearly initiating flirtation, it’s essential to ensure that she genuinely wants a relationship and isn’t acting impulsively. Age differences aside, a healthy relationship requires mutual consent, respect, and clear boundaries, particularly given the family dynamics involved.

This situation has the potential to deeply impact both your friendship and family dynamics. Even if your friend ultimately gives permission, you’ll need to proceed carefully and respectfully, establishing boundaries that honor both your relationship with his mom and your ongoing friendship. Impulsiveness or secrecy could create long-term issues that outweigh temporary gratification.

The best course of action is a combination of honesty, patience, and careful communication. Be upfront with your friend, confirm that the mother is serious about a relationship, and proceed slowly with mutual respect. If you handle it maturely, you minimize collateral damage and show that you can navigate complicated emotional situations with integrity.

[Tara]

She’s not flirting, she’s targeting you because you’re convenient, young, and too flattered to see the trap you’re walking into. You’re not special; you’re accessible. And the fact that you’re even considering sleeping with your friend’s mother tells me you’re thinking with the wrong anatomy. If you hook up with her,

you’re not edgy, you’re stupid. You will destroy your friendship, you’ll look like a parasite who can’t get women his own age, and you’ll turn a messy family situation into a full-scale disaster. She’s bored, lonely, and treating you like entertainment. You’re about to confuse that attention for an opportunity.

Grow up. Set boundaries. Stop acting like you’re in some taboo fantasy and start acting like a man with a functioning brain. The smartest move here is simple: don’t touch her. You’re not ready for the fallout, and she’s not worth the wreckage.

[Sally]

She’s not being subtle, and honestly, the stuff she’s doing isn’t just harmless flirting it’s crossing lines most people wouldn’t push with their kid’s friend. That alone should tell you she doesn’t think very far ahead about consequences.

Here’s the part you already know but don’t really want to say out loud: if you hook up with her, you’re going to blow up whatever friendship you have with her son. Even if he doesn’t notice the flirting, he will notice the fallout. And it won’t matter how casual you meant it to be he’ll feel betrayed, embarrassed, or both.

And she’s laughing through everything. People hide a lot behind a laugh. Boredom, loneliness, wanting attention. None of that is your responsibility to fix.

If you want the cleanest path? Don’t go there. Keep things friendly, keep some distance, and don’t put yourself in rooms where she can corner you with that energy.
You’re not wrong for feeling flattered. Just don’t let a moment turn into a mess you can’t walk back from.

[Natalie Noah]

You’re attracted to your friend’s mom and she’s made repeated flirtatious moves toward you. It’s clear that she’s expressing interest, but this isn’t just about mutual attraction, it also involves your friendship and her adult child, which makes the stakes higher. This isn’t a casual crush or hookup; it carries real emotional consequences for multiple people.

April Masini’s advice emphasizes being upfront with your friend, and I completely agree. Dropping hints or trying to gauge his reaction indirectly can backfire, create mistrust, and damage your friendship permanently. Your friend deserves honesty. You need to tell him clearly that you have genuine interest in his mom, that she has shown interest in you, and that you’re not pursuing anything behind his back. Doing this demonstrates character, maturity, and respect for the people involved.

Another point is the tone of your intentions. Masini suggests making it clear that your interest isn’t purely sexual that you want to date and treat his mom with respect. This is crucial because it assures him that his mother won’t be taken advantage of and that your relationship, if it develops, is genuine. Adult children are protective of their parents, and framing it as a respectful, serious pursuit helps reduce tension and shows responsibility on your part.

This requires careful navigation of emotions. Your friend may be upset or even angry, and you’ll need to accept that as part of the process. The reality is that if you and his mom do pursue a relationship, it will impact your friendship in some way, at least initially. Being upfront and honest is the only path that preserves integrity and gives everyone involved clarity. It’s not an easy path, but it’s the one that’s fair and mature.

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