True Romance: A Friend's Mom Is Hitting On Me, Dad's Having An Affair & Another Relationship Suggestion Fail

We're back for another of our Thursday walks through the world of True Romance. This week we've got some horned-up middle-aged parents out in the wild. One who is hinting at a possible affair and another who has already gone down that road.

Is it an attempt to regain some of their lost youth? Are they having or on the verge of having a midlife crisis? How am I supposed to know? What am I, a psychologist?

That's not how we roll around here. We bury most of our feelings deep down, then proceed with wide eyes as if we're completely obvious to anything that could go wrong. Why? Because that's a lot more fun.

We're not grabbing any tissues to cry in. Now bury those feelings deep, take a nice big breath, and let's unpack this week of fun and adventure.

First up, we have a guy in his 20s whose friend's mom is starting to flirt out in the open with him. You know, not just a look here or there or being over-the-top nice. His friend's mom is saying things in front of his friend and his friend's dad.

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As much fun as that is, we then get into a concerned daughter who uncovered her dad's affair with a much younger, possibly unstable, woman. Can't dad have just a little fun for once?

This week's edition ends with a proposal for an open relationship that now seems like a bad idea to the one who suggested it after he realized that his girlfriend could dump him if she found someone else. Who knew that was a possibility?

A friend’s mom is hitting on me

A 26-year-old took his friend up on an invitation to spend the day in Chicago. His friend and his friend's parents, who this guy has known since he was 9, headed out for a day in the city.

He had no idea what was coming his way during the day out in Chicago. Sure, he had always thought that his friend's mom, now 56, was hot. He admitted that, "he has caught me checking her out in the past."

He even wrote on Reddit that she had, in the past, "gone out of her way to make conversation with me."

That couldn’t have prepared him for what was about to take place, in front of his friend and his friend's dad, on the train that day. His friend's mom said that she liked his Cubs World Series t-shirt. Innocent enough, until she finished that thought.

A 26-year-old man says his friend's mom kept flirting with him in front of her husband and son. (Image Credit: Getty)

She added that "it matched a Cubs bra and thong that she owned." This had him trying to figure out what was going on. He was completely caught off guard. Bra and thong talk in front of her friend and his dad?

There have been flirty comments before, but not like this. This was a "no mixed signals out in the open flirting" the likes he had never seen. His friend laughed it off.

Her husband did not. He "didn’t seem to be thrilled by the comment and a bit embarrassed." The 26-year-old kept it together and replied that they "both had good taste and that I was sure her apparel looked much better than mine."

That was the ice-breaker exchange that opened the rest of the day to stares between the two, and his friend's mom periodically went out of her way to brush up against him.

"Having this happen right in front of my friend and his dad was a bit uncomfortable, but at the same time I found myself becoming very turned on by her," he admitted as he sought advice.

Now most people would say he needs to leave it alone. That's the responsible thing to do after all and that's the feedback he received.

But most people lack adventure and excitement. I'm not saying he should run out and hook up with his friend's mom and ruin a family or anything.

I am saying, however, that if she's flirting that hard with you in front of her husband and son, that the marriage is already in trouble and closing the door entirely on the friend's mom would be rude. Nobody wants to be rude.

This Week in True Romance:

Dad is having an affair with a girl who is basically my age, not sure who to talk to?

I warned you ahead of time that the middle-aged folks were horned-up in the wild this week. This dad is one of them, and he's not flirting with his daughter's friend, he's having a full-blown affair with a 20-something who is pretty much his daughter's age.

His daughter, 24, put it all together that her dad was seeing his 26-year-old coworker on the side. To add some fun to the whole mix, the mistress has borderline personality disorder.

That has the daughter concerned. As she revealed on Reddit, "she’s made threats to tell my mom about the affair, has driven by my family’s home at night, and has asked my dad for money for her mortgage."

After confirming that there were some extramarital adventures taking place, she decided to confront her dad about it. Her mom has her own issues she's dealing with, and she didn’t want to send her over the deep end with news of the affair.

A man's daughter is concerned after discovering his affair with a much younger woman. (Image Credit: Getty)

Dad made it seem like he was "stuck between a rock and a hard place." That's the picture he painted for his daughter. He had a much different version which he told her sister's boyfriend.

He said his daughter needed to watch herself. He likes his mistress because she "actually wants to go out and do stuff unlike my wife" and "she’s blonde with a big butt." 

You have to hand it to dad here. He knows what's important. His daughter described her as having "fried blonde hair and a giant face tat." She doesn't fit the description of someone she "would have pegged him to have an affair with." 

Judging from the "she's blonde with a big butt" comment, it's safe to assume he normally has a much more sophisticated taste in ladies. The bottom line is that dad isn’t giving up the affair anytime soon, and she's worried about what the mistress might do.

"I am concerned that this girl is going to come to my family’s home and confront my mother, and I want there to be a way to stop it before it happens," she admitted. "Is going no contact with my dad and leaving this all to blow up the best solution? Trying to find ways to have the least fallout."

Here's an idea. I know it sounds crazy, but what about minding your own business? Dad is in his mid-40s. Can't he have a little fun without everyone getting on his case?

Let the man live. I'm a big cross bridges when you get to them guy. Who knows how it will end? Grab some popcorn and watch it all unfold.

I proposed to my girlfriend the idea of an open relationship, now I feel bad

Now we end the week with another failed relationship suggestion. It always seems like a good idea until it actually happens. This guy was so focused on an open relationship and sleeping with other people that he forgot that she gets a turn too.

After four years together and a decrease in time in the sheets over that time, this genius came up with a solution. All they had to do for him to get more action was open up the relationship.

He didn’t want to leave his love after all. She just wasn’t getting it done all the way every time for him anymore. That's when he came up with his proposal.

"I love her so much, leaving her was never an option. I never met anybody like her, she is fantastic in every aspect of her life, the world is been cruel to her but she hasn't lost her's spark," he said. "We started talking about an open relationship, we both agreed that it could be done."

A man suggests an open relationship with his girlfriend then has second thoughts when it was her turn to find a partner. (Image Credit: Getty)

That's the perfect solution. He quickly met someone on a BDSM app. They hooked up and that was that. He and his girlfriend continued their relationship and even found out that she liked the idea of him sleeping with other women.

Everything was great until she installed Tinder. She started to talk to another guy on the app because, "she expressed the need to know him before sex and to keep having sex with him as friends, because it seemed more natural to her."

Now this seemed like something completely different from what he was up to, and he's now worried. He thinks he might have messed up and that there's a possibility that "she will fall in love with someone now or later and dump me."

I'm not going to kick a guy when he's down by suggesting he should have thought of that beforehand. That's for him to figure out. What are the chances she leaves him anyway?

He talked about his concerns with her, and she said, "that it can't happen because she loves me more than she ever did. I believe her, but I'm not feeling better. You can't see things like this coming in advance."

That's true. You can't see things coming in advance. But she told you that it's not going to happen. You guys set up rules. There's nothing to worry about. She's "happier these days" now that she has a new person in her life.

So opening up your relationship and having your girlfriend find happiness with a "friend with benefits" might be a bad idea. It could be worse. She could slowly be leaving you for someone else behind your back.

This way, she's doing it right in your face. Best of luck.

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That's all we have for this week's True Romance. Follow along on Twitter and feel free to send questions, comments, stories, and whatever else you like my way. The inbox is always open, even for those who don't understand sarcasm, sean.joseph@outkick.com.