[Dominicana79]

Recently in the last year have been talking more eventually leading to outings that involved our 16 year old daughters. The first two and half years that I have known this man, I was never attracted to him. And then something in the last 6 months clicked and we became very close, including sharing intimate details of our personal lives. When we’re together we have this intense connection that is more than anything I have ever felt. He has had many girlfriends but they all turned out they just wanted to try and see what being with a man was like, but all left him for a woman. And I haven’t dated or been with anyone since I first got separated from my husband 14 years ago.
He sent me a message about 4 months ago stating that the girls really want us together and for me to think about us starting a relationship. The next day, he said that he was drinking and doesn’t remember but he didn’t deny what he had written. He planned two outings with our daughters which was a blast, including one night where he cooked for us and we had a great night. He is super shy and hasn’t made any moves. We recently went on a 10 hour trip to the Bay Area and there were many opportunities for him to make a move but her didn’t. He is always lending a hand to help me with stuff around the house that needs to be fixed. I’m always the one starting conversations via message, well about 90%.
Do you think he is really shy and just doesn’t want to mess up what we have going on so far? Is he even interested? Am I wasting my time?

[AskApril Masini]

There’s something missing here…. he hasn’t really approached you as a date. 😉 It sounds like he’s looking for a ready made family that he can join and match with his — but it’s very important that the two of you have a romantic connection beyond his making dinner for you and the kids and doing things with and for the kids. It sounds like he may be using the kids to leverage his relationship with you, and I think you need to wait and see if he asks you out on a date and if the two of you can have a romantic relationship without the kids around. Dating is a scary prospect for a lot of people — especially those who feel burned by a divorce. So, he may be trying to avoid getting hurt and that’s why he’s kind of backing into this relationship instead of going into it face first. The reality is that you can’t protect yourself from hurt — it happens. There’s no love insurance. 🙂 And once he realizes this, he may be more interested in trying to have a romance with you, come what may, and that’s when you’ll know that he’s not just interested — but he’s ready.

I hope that helps.

[Sally]

This kind of situation messes with your head.
From the outside, it does sound like he cares. He makes time, plans things, helps you out, and that message he sent wasn’t nothing, even if he tried to brush it off the next day. People don’t accidentally write stuff like that unless it’s already living in their head.
At the same time, his actions are very cautious. No moves, you starting most conversations, him not really stepping forward. That can be shyness, or fear, or him being unsure what he wants. Especially if he’s been hurt before, he might be scared to cross a line.
I don’t think you’re wasting your time, but I do think you’re carrying more of the emotional weight. At some point, it’s okay to gently ask where his head is at. You deserve clarity, not just chemistry.

[Tara]

Shyness is an excuse people use to protect hope. A midlife man who has dated, traveled, raised a child, managed relationships, and survived multiple breakups does not suddenly forget how to express interest. He knows exactly how to make a move. He hasn’t because he doesn’t want to deal with the consequences of wanting you.

Let’s dismantle the fantasy. He sent one emotionally loaded message while drinking, then immediately walked it back. That wasn’t vulnerability, that was impulse without accountability. Since then? No escalation. No clarity. No pursuit. Just companionship, favors, and plausible deniability.

Ten-hour trip. Private time. Emotional intimacy. Zero action. That is not a restraint. That is indecision. And indecision is a decision.
You are doing the emotional labor, the initiating, the wondering, the waiting. That tells you everything. Men don’t sit on their hands for six months when they feel “the strongest connection of their life.” They move. Especially at his age. Especially when children are involved. Especially when the stakes are real.

His history matters too. A man repeatedly chosen and then left isn’t unlucky; he’s unresolved. And you, after 14 years alone, are vulnerable to mistaking intensity for meaning and familiarity for safety.

Right now, he gets companionship, validation, help, emotional closeness, and zero risk. You get ambiguity and hope. That’s not a connection. That’s a convenience.
You are wasting your time if you’re stuck living in limbo, reading signals, and romanticizing silence. If you want clarity, you stop circling and say one direct sentence asking where this is going. If he hesitates, deflects, or stalls, you walk. No drama. No analysis. No more house projects.

[Member]

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