Alias (DO NOT USE A REAL NAME!!): susan
Comment: I’ve been dating a widower for 10 months and we have
only had sex once, I have roommates and he lives with his daughter so location is a factor. We have gone to hotels but he was impotent.
A few weeks ago, we went to visit my daughter and took her and her boyfriend out
for dinner, the whole trip probably ran about 1,500
he likes to spend money, though he is not rich, I think it makes him feel important. I felt obligated because of the big expense and we managed to have sex, I didn’t enjoy it. He seems to be very needy, was married for 40 years and faithful. but his wife
passed away a year ago. I kept telling him that
he is trying to fill the void, he comes on so strong
with all his very romantic outpourings, and wants me
to say I love him..I can’t..
The real problem is that I started sleeping with my
roommate, who is a little younger then the widow and
is going through a divorce. He has been living
with me for a year and we talk all the time, watch
TV, and sometimes go out to a party or a jazz club.
A few weeks ago he knocked on my door and wanted to
cuddle which ended up in sex, since then we have
had sex 5 more times, each time hotter and hotter.
I feel like a bad person because the widower claims
that he is in love, but I only see him once a week as he he is very involved with his kids and in laws.
I’ve never seen him on holidays.
A friend of mine said I am wasting my time with
the roommate, that he is not boyfriend material.
I wonder if being practical is that important, and pretend to like kissing the widower? or continue with the roommate? We are planning on going to several seminars in real estate, and talk about building up an investment business, the field he is in now.
At least he is very motivating and very easy
to get along with…
City: New yORK
You’ve written in a few times before, and I have to say that I pray that I’m as active as you appear to be when I hit my sixties. You date more than most women I know that are my age.
That said, I don’t get a good feeling from this roommate. I’m basing my opinion not just on this letter but the one you submitted previously.
My sense is that you get targeted by guys looking for a Sugar Mama. Something tells me that you keep meeting men (usually much younger than you) who can’t support themselves and are seeking someone who will help them along financially. The minute someone you barely know starts talking money, you should be hightailing it out the door.
Your roommate, who is probably stretched quite thin monetarily due to his impending divorce, sounds like he may be looking for a benefactor. I say this because you and he are discussing a business venture together, one that he undoubtedly needs capital for and can not raise himself. This guy is bad news. He can’t even rent an apartment for himself. That’s how broke he is.
As for the other guy, you don’t seem terribly interested in him, so why bother keeping up the charade? I get the sense that you want someone more vibrant. The problem is that you keep finding that quality in douchebags.
I can’t tell you what you should prioritize. Practicality doesn’t appear to be a thing for you. From what you’ve shared, you give the impression that you’re attracted to younger guys, or at least men who have something flashy about them. Or maybe you’re just drawn to the intrigue. I don’t know. What’s troubling to me is that your radar doesn’t appear to have improved.
If you keep this fling up with your roommate, I can almost guarantee that he’ll disappear once you’ve funded him. He’s sketchy. I would do what you can to cut things off.
You need to decide what is more important – chemistry or companionship. If it’s chemistry, you can date and sleep with whomever you choose. Just be smart about it. Guys who are having a hard time getting by should be an automatic No for you. But if it’s companionship then I think you need to adjust your expectations. Real talk: sexual dysfunction is common in men and women over 50.
I totally get your desire to be sexually fulfilled, but I think as we get older we need to re-evaluate what it is that’s truly important.
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