Dating at Midlife/Am I too nervous


Sorry this is so long!

I met a man a couple of years ago through work - our companies partnered with each other now & then. We live about 6 hrs from each other but he had to travel frequently. So, things progressed very slowly & we began to do things just as friends when he'd pass through town. Hikes, out to dinner etc. I had him over for dinner a couple of times- I figured restaurant food must get pretty old when you're doing it so often.

So, after about 9 months of this he did spend the night. About 3 weeks later I was working near his town so went & stayed with him for a night. Things got kind of confusing for me- he stayed with me one more time & then just pulled back from sex to just wanting to be friends again. We never really talked about why that happened.

I made it clear that I wanted more but was ok being just a friend. He kept on flirting with me like wanting to give me a hug when he come to town, complimenting me a lot etc.. I really came down hard on him about not giving me mixed signals.

Then we didn't see each other from Sept. to June although we talked & emailed a couple times a month. He stopped traveling so much so didn't pass through here. Then he left his job last winter so we didn't have that between us.

Ok fast forward to this summer.

I was visiting with an acquaintance from another town (not where he lived) & she told me she was dating him. I was surprised but didn't say anything. A few weeks later he called me saying he was coming through my town & wondered if I was going to be around for hiking, fishing etc. Since he's no longer with the company he was stayed at my house.

We ended up laying on the guest bed when I jumped him about the other woman. He said it wasn't really a relationship etc. Well, I got up & went to sleep in my room. We had a nice rest of the visit but I told him I didn't want to play games & have him hurt her.

Then a couple of weeks ago he came all the way up to my place (a 6 hour drive) for hiking fishing etc with me- at his instigation. I was really confused but didn't have the guts to ask him on the phone about what he wanted & had the guest bed ready. He ended up telling me it wasn't what she thought it was & he'd had talked to her (broken up). So we slept together & he stayed for 3 days.

We did talk about what was going on- I told him I didn't want to play games, I wasn't sure where this was going, but didn't want to be involved if there were any other women.

I told him that I'd laid down the cards last year about wanting him but being ok with being friends. So now he's talking about a wanting a dating relationship with me rather than just friends. Throughout the whole thing we've really enjoyed each others company & like doing the same things together- hiking fishing skiing etc.

I'm really happy but also really worried. We've had a couple of long talks while he was here & then over the phone. I asked him what changed & that I'm confused, but don't feel I've gotten a really clear answer. But I wonder if I'm just being really nervous about getting hurt. He tells me I'm really attractive we like doing things together etc. and seem like a really good match for each other.

I wonder if I'm just being hyper worried that he's just playing around with me- testing whether he wants to be with someone & sees me as a good try for that. Or maybe he really has changed his feelings.

He said he's worried about a long distance relationship. In all honesty, I've been single long enough, my daughter's gone off to college & I'm not sure I want to have someone else living in my house- give up that freedom- so think I might like that, at least to begin. He's looking at taking a job closer to me, but still a few hours away.

Do I just have my head in the clouds? I'm I too nervous or not reading him that he really does want to be dating?

Also I'm 53 & he's 63 so this isn't a brand new thing for either of us.

Hi Carol, I'm not sure who doesn't want this relationship. You're fearful about giving up freedom and space. He's concerned about long distance relationships. You both have valid concerns. Relationships are challenging enough but without 100% conviction there's sure to be issues. I think that there has been a lot of issue skirting. That can't happen in solid relationships. Trust and communication are paramount to a relationship. You never came out 100% that you want a relationship. You couched it with a friendship and told him that was okay but your actions ( sleeping with him) said something else. He never came out strongly for the relationship as I think he was confused. Fast forward today
You have to believe  that there are no games and this man is sincere. If you have any doubt discuss it until you're both blue, but be sure of what you want and what your'e getting. Finding love at our age is awesome but understanding compromise and integrity is essential.
Best of luck in  your decision.

Dating at Midlife

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Lauren Stevens


I can answer all questions pertaining to dating, dating at 50+, online dating, health and sexual issues regarding relationships.


I have been a life coach and all expert coach for over 15 years.

I have founded and facilitated Life After Divorce a coaching program that promotes and enables life changing events. I also facilitated Transitions a support group for the traumatic experience of people going through divorce and the newly divorced.

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