[jade]

I am a 57 year old woman. I am physically active with a lot of energy and ride a bike with a bike club. Through the club, I have met many new people over the past three years. We go on rides together, socialize, and often develop friendships “off-bike.” It has been fantastic for me. There is one man, “R”, also age 57, who I have gotten to know through group rides and off-riding activities over the past year. We recently went away for the weekend with two other riding friends (the two women sharing a room and the two guys sharing) and had a great time riding, eating out, going to the beach, laughing, talking, and just having fun. I knew R liked me and I have had a crush on him on and off, but I had recently found out (one month ago) that he lived with a woman whom he had called his “landlady”. He didn’t come right out and say anything, but basically confirmed that she was more than his landlady. On the recent weekend trip, R told me he was in love with me and that he and his partner were not intimate and hadn’t been for ten of the twenty years they had been together, but when I asked, he did admit that they shared a bedroom. 🙄 He said that he had always used his head in relationships all his life and now he was using his heart. (Coincidentally, I am NOW using my head but the reverse was probably true in the past, go figure!). He said he wished he had met me 40 years ago, etc. He basically said that he and I have never even kissed let alone anything else more intimate, and therefore he wasn’t sure about moving out from a situation housing-wise that is comfortable (low rent, plenty of room in house R resides in with the woman (who owns it), basement space for his metal-work shop, etc.). It appears he wants some assurance from me about being liked or wanting a relationship with him. I told him that I really liked him, but I expressed misgivings about becoming involved with someone who was still in a relationship (of some kind) with someone and/or living with them. We did kiss and hold hands that weekend when the other two friends weren’t looking but having had a bit of time to think about it away from the weekend, I guess I would need him to actually move out or put some closure on that situation. Otherwise, if I got involved, I could forsee us being intimate, then R leaving and going home to the “landlady.” I know that would never work for me. It seems that we are at a stalemate. He wants me to see him and get to know him better and even be intimate and I do not want to fall for someone who is living with someone else even if that relationship is dead. I have lots of fun flirting and bantering with him, and he really makes me laugh, he is sweet, have-your-back kind of guy. Any advice? I have not been in a relationship for three years, but recently due to all the fun I have been having, a lot of guys have shown interest in me and one (who, admittedly lives quite far away) wants to take me to dinner in October when he visits my state. Do you have any advice about this situation, and honestly, I want to know if I am doing the “right” thing. Am I being too exacting about this at my age? Should I just leap?

[Ask April Masini]

You’re definitely doing the right thing. You may be having some fun, but you can definitely do better for yourself than this guy. 😉

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[ebonypittman88]

You are in the right track jade. Enjoy , have fun , don’t limit yourself in the four corner of your room.
That man you are talking give him a chance to see you. Who knows you can be a better partner:)

[jade]

Thank you April and ebonypittman88 for your replies. April, would your response be different if he moved out and had his own place?

[Ask April Masini]

Yes. A guy who’s living with a woman (and sharing a bed with her) isn’t as available for a monogamous relationship as a guy who’s single in every way. 😉

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[jade]

So R moved out last weekend and now has his own apartment. He said he told his girlfriend he was moving out last Friday. He said she was upset and did not go to work that day. He said she helped him pack some of his stuff and they were together for the weekend. When I asked if he still had a key to the place he shared with the girlfriend, he did not reply. He said he still had things there. He had originally said he was going to move all of those things into a storage unit. He now says he has not used them in the past year. It seems to me he hasn’t moved everything out. I know he had a metal shop of some type in the basement. He had originally told me he had stuff on all four floors of the house because he’s lived there 20 years.

I agreed to have dinner with him tomorrow night. I am getting cold feet for the third time in the past month about this situation. I like him, but don’t know whether to see him or not. I don’t want drama and I don’t really know what his situation is with the (now ‘x’?) girlfriend. What should I do? Should I meet him? Should I find out more? Should I just say forget about it? I’ve told him three times I don’t think this is going to work and he keeps calling me. I want to try but I don’t want to get into a situation where there is unnecessary drama. All my friends and family are telling me to forget about it. What should I do?

[Ask April Masini]

Your gut is telling you what to do. Listen to it. Let him know that you want to wait until he’s completely single before you commit to a date! 😉

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[jade]

SO, I explained to R that I wanted to wait until he was completely single before committing to a date. And that meant he was fully moved out and the key was returned to his former girlfriend. We spoke for about 40 minutes with him trying to convince me to see him before that. He ended up telling me that yes, he still had a key and yes, he has been to the former girlfriend’s house several times this week to bring more things over to his new apt, and it would take about three weeks to get all his remaining stuff there moved to a storage unit, and that he loved me so much and could not live without me, and there are beautiful women walking down the street and he sees them but isn’t interested in them, and he has been waiting his whole life for someone like me, and that I am being completely unreasonable. And he doesn’t see the problem in just having a hamburger with him. I held firm and he ended the phone conversation by saying he didn’t know if he could live that long (the three weeks it will take to move all the remaining stuff into storage) and goodbye.

I know I have to have a specific question and I know I probably just want confirmation again of my gut feeling about all of this, and you’ll probably give me a really short answer and I understand why (there is only so much advice you can give any one person!) but I wish you would please comment here. Am I being unreasonable? Is this a difference in, as you say with some situations, compatibility? Or what are our differences? Would most people just go on the date?

[Ask April Masini]

[quote]Am I being unreasonable?[/quote]

No.

[quote]Is this a difference in, as you say with some situations, compatibility? Or what are our differences? [/quote]

He’s not really single yet. You want someone who’s really single. That’s a compatibility difference.

[quote] Would most people just go on the date?[/quote]

I don’t know, and I’m not sure why you care about most people. You should just focus on what’s right for you. 😉

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[Ethan Morales]

You’re not being picky, you’re being sane. At 57, you know what you want and what you won’t tolerate, and that’s worth protecting. R’s living situation sounds like emotional limbo, not closure. Kissing and hand-holding while still sharing a house and a bedroom with someone else, even a “dead” relationship, is a setup for shame, secrecy, or future hurt. You already spotted the most likely outcome: intimacy with him, followed by him “going home.” That’s a lousy equation for a grown-up romance.

Put a boundary in plain language and let it do the work. If you want to move forward with him, require a concrete step he moves out, or he ends the house-situation and gives you a clear timeline and proof of that choice. Not because you want to micromanage his life, but because you deserve clarity before you invest emotionally and physically. Ask for a short, sensible timeline (weeks, not years). If he can’t or won’t do that, step back; flirting and weekend kisses are fine as long as you treat them as exactly that fun, not the start of something official.

Don’t stop living your life while he figures it out. Keep seeing people, keep the October dinner on the table if it sparks you, keep your bike club adventures. You’ve got options and agency; leaning into them will keep you from being the consolation prize. Let him show he values you enough to make a clean choice words and wistful wishes aren’t the same as action.

Trust your gut. You already answered the important question you need closure on his past before starting a future with him. If he loves you, he’ll act. If he doesn’t, you’ll save months of heartache by walking away now. Either way, you stay true to yourself, and that’s the right thing.

[Sally]

You’re not a teenager you’ve lived enough life to know when something smells a little off, even if the feelings are real and the chemistry is fun.
Here’s the thing… men don’t stay in someone’s house, in someone’s bed, for twenty years by accident. Even if the romance died ages ago, that situation is still comfort, still dependency, still a whole tangled life you’d be stepping into. And you already know you can’t be the woman he kisses on weekends and then goes “home” to someone else. That would eat you alive.

You’re not being too exacting. You’re being honest about what you need to feel safe and respected. At 57, you’ve earned the right to want clarity, not complications.
If he wants something real with you, he’ll take the grown-up step and move out. Until then, enjoy the flirting, enjoy your bike rides, enjoy the attention from other men but don’t leap into something that already has red flags waving.

You’re not wrong. You’re protecting your peace, and that’s worth more than a sweet weekend kiss.

[Natalie Noah]

You’re being very thoughtful and cautious, which is exactly what you should be doing. Your instincts about wanting a fully available partner are healthy. he’s only just moved out, and the lingering ties to his previous relationship create uncertainty and potential for drama. Jumping into dating him now could put you in a position where emotions run high while the past isn’t fully resolved, which would make things messy and stressful for you. It’s completely reasonable to wait until he is fully single and independent before committing to a date.

It’s also about compatibility and boundaries. You’ve recognized that you need clarity and security in a relationship, and that’s not unreasonable or overly exacting, it’s self-respect. Compatibility isn’t just about having fun together or feeling chemistry; it’s also about timing, commitment, and ensuring both parties are emotionally ready. Right now, he is still tied up in the logistics and emotions of leaving a long-term living situation, so there’s a mismatch in availability and readiness between the two of you.

The best course of action is to honor your boundaries and trust your gut, as April advised. Waiting until he’s completely free and settled isn’t about being inflexible. it’s about protecting yourself and creating the foundation for a healthy, drama-free relationship. You can still maintain some connection, but letting him know your terms clearly (full single status before dating) ensures that you’re prioritizing your own emotional safety and long-term happiness. Anything less would risk unnecessary complications that could have been avoided.

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