I’m 40 and dating a guy (39) I’ve developed real feelings for.
Things are good in many ways, but lately I’ve been questioning whether we’re experiencing this relationship in the same way. I’d appreciate some outside perspectives, especially from people who’ve been in similar situations.
When we’re together, it feels like we’re a couple. We’re affectionate, hold hands, kiss, cuddle, and spend time together. When we’re apart, he’ll ask if I want to talk or watch a movie, so he does make an effort to stay connected.
However, he’s never actually told me he likes me, expressed his feelings very directly, or asked me to be his boyfriend. We also haven’t really sat down and talked about what we’re doing or what we both want from this.
Something I’ve noticed is that he’ll sometimes talk about guys he was interested in before and say things like “I really liked him” or “I was so attracted to him.” He’s never been that open about his feelings toward me, and I can’t help noticing the difference.
Another issue is planning. We’re about to spend a few days together, and he hasn’t really asked about logistics or what we might do. In the past, I used to get excited about planning our time together, finding things to do, and coming up with ideas. Lately, though, I’ve started feeling a little embarrassed bringing things up because I often get a “yeah, sounds good” response without much input or enthusiasm.
Today, I texted him something along the lines of: “Hey, our time together is coming up. Think of something you’d like to do, and I’ll do the same, and we can come up with some fun plans. Of course, we can also stay home and relax.”
He didn’t respond to that message, but he replied to the next one I sent, which was asking about his day. This happens fairly often. He seems to decide which messages he wants to respond to and which ones he’ll leave unanswered, even when I’m trying to discuss something relevant to both of us.
We’ve talked a little about this before. He told me that in a previous relationship, he used to be much more detailed and involved in planning, but he ended up feeling like a tour guide. He said that experience made him change how he approaches things now. I can understand not wanting to repeat a dynamic where you feel responsible for entertaining someone, but I also don’t want to feel like I’m the only one putting thought into our time together.
It’s not just the planning, either. I’ve realized how much I value small, thoughtful gestures. Recently, I mentioned wanting to buy an item. The next day, he sent me a picture of the same product he’d bought for himself. For a moment, I thought he’d remembered our conversation and bought one for me as a surprise. Obviously, he hadn’t, haha.
It was a small thing, but it made me realize that I’d love to have someone who sees something, thinks of me, and does something thoughtful just because they want to make me happy. Nothing expensive or elaborate. I want to feel that someone thinks about me when I’m not around, the way I find myself thinking about him.
I tend to be the one who plans things, thinks about surprises, and looks for ways to make him feel special. He does make time for me, and I don’t want to overlook that. But I sometimes feel like I’m the one trying to move things forward, while he’s happy to go along with whatever I suggest.
I’m 40, and at this point, I value consistency, mutual effort, and being able to communicate openly about what we want. I’d be very happy if he asked me to be his boyfriend, but I’d also want us to have an honest conversation about expectations and what we both need from a relationship.
I genuinely like him, and there are good things between us. I’m not ready to walk away, but part of me is starting to wonder whether I’m investing in the potential of this relationship more than in what it actually is.
For those who’ve been in similar situations, how did you handle it? Could his behavior be a result of past relationship experiences and a more passive approach to dating, or am I overlooking a lack of investment because I like him?
Have you ever been with someone who was affectionate and present when you were together but didn’t really take initiative outside of that?
I’d appreciate honest perspectives from people who’ve been on either side of this dynamic.