Irish

I’ve been chatting with a guy online for nine months. We’ve been intimate over video calls, he calls me beautiful, and we spend hours talking with loads of emails every day. The issue is, he’s been divorced for two years and says he’s not ready for a relationship. He has two grown daughters and lives in the U.S., while I’m in Ireland. I’m in the process of separating, but he’s made it clear he’d never date a married woman. Am I wasting my time with this?

Here’s the hard truth: yes, you’re wasting your time. This guy’s told you he’s not ready for a relationship, and yet you’re hanging on, hoping he’ll change. Newsflash—he’s enjoying the attention without any commitment, and if he actually wanted something real, he’d make it happen. 

Stop wasting your time with a long-distance relationship when there are plenty of men near you who’d actually appreciate someone ready for the real thing. And let’s be blunt—you’re 44. You don’t have time to wait around on a guy who’s fresh out of a marriage and clearly just looking to get laid. You’re invested, but he’s not, and he’s shown that over and over.

There are plenty of men closer to home who won’t need convincing and who actually want to build something. So cut this guy loose and find someone who’s ready to match your energy. You deserve someone who’s all in—not someone who’s keeping you on the back burner.

White

Hello, I have been engaged for about 3 months, and we’ve been together for almost 3 years. A few times a year, my fiancé goes out with his buddies, saying it’s a guys-only night. However, most of the time, someone brings girls along. While many of his friends are unfaithful to their wives, he claims that’s their issue and insists he isn’t like that. Recently, he went out, and once again, girls were there. He told me it wasn’t his fault and said he prefers being honest with me. I expressed that I don’t think it’s appropriate for an engaged man to go to bars where there are girls. When I asked how he would feel if I did the same, he said, ‘I don’t care, I know you come home to me.’ What should I do? I love him, but I’m not in my 20s, and I’m not sure he’ll ever change. Please help! Thank you.

Alright, here’s the deal. You’re 44, not 24, and you’re looking for stability, not excuses. Your fiancé going out with his boys isn’t the issue—it’s the fact that these “guys’ nights” always seem to end up with women joining, and he doesn’t see that as a problem. That’s a red flag, plain and simple. The fact that most of his friends cheat and he just brushes it off like it’s their issue? Come on, he’s putting himself in situations where temptation is always around and you can bet he’s also participating!

Now, when he says, “I don’t care, I know you come home to me,” that’s a cop-out. It sounds nice, but it’s just a way to shut down the conversation and avoid accountability. You’re not in your 20s, playing around and hoping he’ll mature. You’re a grown woman, and you need to know if he’s going to step up and be serious or keep acting like he’s single.

If he isn’t willing to respect your concerns and adjust his behavior, you need to think long and hard about whether this is the man you want as your husband. Love’s great, but trust and mutual respect are non-negotiable. So, what should you do? Lay it out straight. Tell him exactly how this makes you feel and that it’s not just about trusting him—it’s about the kind of life and respect you want in a marriage. If he’s not on board, then you’ve got your answer. Don’t waste your time hoping he’ll change if he’s not willing to make that commitment now. Be smart.

Latina

I recently met a man at a car service center who fixed my car and didn’t charge me. I was surprised, but then the following week, I returned for another repair, and he once again didn’t charge me, saying all he wanted was a hug and calling me beautiful. This seemed strange, especially since I felt I looked my worst. Why would he do this and only ask for a hug in return? What’s really going on here?

Look, at 60, you’re not turning heads like you used to, unless you’re some exception like Madonna. This dude at the mechanic shop? He’s probably seeing you as an easy mark. He’s flirting with you and playing the nice guy card to see if he can get his foot in the door. Guys who aren’t making much money—like a mechanic who doesn’t own the place—will sometimes look for a way to upgrade their lives. If you’re rolling up in a nice car, he’s already thinking, “Okay, she’s got money.”

And let’s be real—single women at 60 can sometimes crave companionship, and he’s betting on you being one of them. Don’t be that woman who gets suckered into buying him stuff or letting him freeload. Before you know it, he’ll be hinting about needing help with bills or worse, trying to move in. If you’re interested in him, fine, but don’t make it easy. Make him prove he’s not just after your wallet or a comfortable ride. Don’t fall for the sweet talk and compliments.

Bottom line: don’t be naïve. Guard your heart and your bank account, and don’t let loneliness make you do something you’ll regret. Be smart and watch your back.

Mixed

Hi, I’ve known this guy for years, and recently we’ve started talking a lot more. We’ve both liked each other at different times in the past, but the timing was never right. Now, it feels different, but I can’t tell if he’s just being friendly or if he wants more, especially given our ten-year friendship. He recently bought me flowers, and last night he called me gorgeous, saying he’s always thought so. But he hasn’t asked me out, and I’m unsure of his intentions. It’s been a while since I dated anyone, and I’ve never dated a friend, so I’m confused. Any advice? Thanks!

The ten-year friendship?

Forget about it for a second. If a guy is buying you flowers and calling you “gorgeous,” trust me—he’s not just trying to be friendly. Guys don’t pull out the compliments and flowers routine for someone they only see as a buddy. He’s trying to make it clear he’s into you, but he’s playing it cautious because he has been in the friend zone for so long. He’s testing the waters here, giving you these big signals without diving in headfirst, hoping you’ll pick up what he’s putting down.

He hasn’t made a move because he’s probably worried about wrecking what you two have if it doesn’t go his way. But here’s the reality: if he liked you back then, he likes you now. Guys don’t just drop those feelings, especially when they’ve been low-key carrying a torch for you all these years. So if you’re even a little bit interested, start giving him a sign. Lean into the flirting, make it obvious you’re open to more than just friendship. That way, he knows it’s safe to ask you out without thinking he’s about to nuke a decade of friendship.

Bottom line?

Stop overthinking it. If you’re into him, show it. And if you’re not, then put it out there so he doesn’t waste his time. But don’t sit there confused when he’s all but waving a neon sign saying he’s interested. Make a move or give him the green light to make his.