Is he flirting? Trying to get my attention?

By the way, I know for a fact he’s not seeing anyone. In fact, all of his/our friends were surprised when we went out for almost 7 months and he introduced me to them and all of his parents. They said they hadn’t seen him with anyone in 15 years since his divorce.

Um, ask him? (Preferably in person.)

You need to talk with him. Ask him what the little signals mean. Tell him how you feel (do you know?).

If it was me and he claimed to be interested, I would really want some reassurance about how serious he is before going down that road again.

I largely avoided communicating with him for the first month or so after the breakup, but yesterday I was feeling sentimental. We have communicated some, although he has not expressed a desire to rekindle. I sent him a message on Facebook: “Something I should have said earlier but never really did: thanks for all those breakfasts you made me.” We spent weekends together, and he always made me breakfast every Sunday morning.

The middle of the day he responded: “Well, I didn’t want you to starve to death at my house. Might be a little hard to explain to the authorities.” Then about 8:30 last night, when I hadn’t replied, he responded a second time: “I enjoyed them also.”

Mixed message for sure. Ask him what he’s about. Most likely a lot of ambivalence which is fairly normal.

Oh, and he also told me that sex with me was nothing like he’d had before—even with his ex-wife. When we split, he made of a point of telling me that the sex was incredible. So it’s not an issue of sexual incompatibility. (I thought it was pretty mind-blowing myself, and that’s been hard to get over.)

How old are you two? I think it’s possible he’s missing you and having second thoughts, and it’s also possible he has nothing else going on now and likes the idea of getting you interested again.

Maybe he liked the sex (only) and is trying to hook up with you again.

To answer jca’s question, I’m 38, and he’s 60. Yes, I know: a 22 year age difference. But he doesn’t look his age, and we have SO much in common, including our musical tastes, agnoticism, love of wine, interest in travel, political sensibilities, political beliefs, and artistic interests—and even our shared habit of sleeping until 11 or 12 on the weekends.

When we became ambivalent and we split, he wrote me a 4-paragraph letter, the 2nd paragraph of which read as follows: “As I’m writing this, I think maybe I need to have my head examined, for you’re a beautiful lady, smart, interesting, we have so many things in common—I couldn’t go to the drawing board and some up with a more ideal woman. And the sex—that’s been pretty incredible. The time I have spent with you has been wonderful.”

I meant above “when HE became ambivalent, and we split…”

If the communication between you two has been so good, it seems like the way to proceed is to ask him what he is thinking.

You asked, so I’m speculating wildly. I like to do that. The less information, the better. I can be completely unbiased about this since I know nothing.

He does want you back. Unfortunately, he doesn’t think he deserves you. You are 22 years younger, for one thing. You deserve someone who can spend the rest of their life with you. Also, he will surely fuck it up. He messed up his marriage and he still hasn’t figured that one out. And he’s 60. His time has gone by. There’s no more love for him now.

Of course, there you are. Smart, and sexy and still available. That’s killing him. He wants to be the one to peel you out of that dress. But he’s voluntarily given you up. Hmm. He wonders if you still want him. But he can’t say that. He can hint and maybe you’ll say something, but he has too much pride to get down on his knees for you.

And besides, if you ask him, maybe he’ll get to reject you all over again. He can be an idiot twice.

Do you want my advice? Well, you’ll get it, anyway.

Reach out to him. Tell him that you still want him and you don’t care how old he is. But if he rejects you again, you’re going to make sure he gets on every junk mailing list in the cosmos. He better not be a jerk. Because he was a jerk the first time. And he owes you. And you’re giving him a chance. One chance. To pay back what he owes and to love the love of his life. Sorry. May sound a bit over the top, but you’ve earned it. He never should have given you up. Very few people get two chances.

I’m sorry. I’d have an I don’t care attitude. I’m giving you a chance and you’ll probably fuck it up, but just in case, I feel I owe it to myself to give you this chance. Just don’t be a jerk.

That’s probably not the best way to set it up, since it invites him to be a jerk, but it’s also a high risk challenge. If he can eat his pride and do the right thing, you win. You’re making it hard for him to win, but that’s good. You want it to be hard. He has to really want it. Otherwise you don’t want to mess with him any more.

That’s what I think.

Based on the story I made up in my head. I’m laughing at myself. I have no idea if this contains anything worth your while. What do you think?

Very good advice, I think, wundayatta. I don’t know who screwed up his first marriage. He said he took her for granted and focused more on their three kids and so she ended up having an affair. He thought something was going on but didn’t know what. Those were pre-Internet days, and he ended up buying a recorder he hooked to the phone and recorded the conversation between his wife and her lover, a man he knew from their high school days. She ended up lying to him later, saying she wasn’t seeing the man anymore, but he knew they were. That experience is why he says he has such defense mechanisms in place.

I think he’s scared of me not just because of the age difference, but because I’m divorced and I initiated it. Early one Friday morning this summer, he texted me, and instead of his usual “good morning, beautiful” or “wake up,” he asked why my husband and I broke up in the first place. It was a weird text to receive because I couldn’t answer it in a reply text, and I texted him back to tell him we would talk about it that night when we were together. I explained to him that night that, although not abusive, my first husband was too controlling and possessive and critical, and I fell out of love with him. I think my initiating my divorce may be a factor in this guy’s fear and subsequent distancing himself from me.

Tell him you’d like to see him. I figure he has at least 20 years to go. Would he prefer to live it with or without you? He obviously misses you.

@wundayatta‘s analysis sounds plausible.
I was on his end of things (minus the age gap) a few months back, where I felt that the relationship was enjoyable but not shaping into a permanent condition. I initiated the breakup, but still kinda miss her; I’d like for us to be friends. Early attempts were interpreted as mixed messages. I don’t see us ever resuming a romantic relationship in the future.

Best way to know, of course, is to ask.

How long did you see each other, nullo? Why did you feel that the relationship was “not shaping into a permanent condition”?

By the way, here is what he said to me about the relationship 2 months ago. I forgot that.

“Something was missing for me. Why, I don’t know. I’m not sure I can explain the reasons. I’m not sure if it had to do with the fact that I hadn’t really had a real relationship in 15 years and the thought of it still kinda scares the hell out of me, if I’d kinda gotten set in my ways during this time, if it’s that I was having a hard time opening after my divorce (I know I have a problem with this; defense mechanism, I guess). It’s certainly nothing you did or didn’t do. All I know is this is what I’m feeling, and it has been troubling me.”

Please post an update as to how things turn out. Best of luck to you on whichever route you decide to take.

JCA
The Update Lady

@femmefatale We dated for a year. She felt distant to me most of the time, never initiating anything. Korean pop culture, particularly its male sex symbols, would inevitably dominate every single conversation. And her life in general; she put so much time into being an e-groupie that she actually started failing her courses in school. She eventually dropped out. I did what I could, helping with the homework, introducing new ideas and activities, even expressing concern, but if it wasn’t Korean boy bands she wasn’t interested. I realized that she wasn’t going to change. After a year, we were as close as another couple might be after a month or so.
I’m still not completely sure that I did the right thing, and it pains me to see her social life devolve into work and church and k-pop. But I figured that this is one of those times where you must worry about your own feelings a little bit.

Thanks, nullo. I was never distant to this man, from my perspective. In fact, he said when we split that he felt guilty because he realized I was putting “more emotion and passion” into the relationship than him and he felt it wasn’t right or fair to me. He said it was “just the emotional hand [he had been] dealt.”

This is someone who told me when we were together that he “didn’t believe in fate but wanted to where [I was] concerned” and we “were made for each other” and that he loved me and cared about me.

Also, only two or three weeks before we split, we were on separate trips (for business), and he was calling me and sending me flirty texts daily. He asked if I had a roommate. I did (a female colleague), and he said, “Wish it were me.”

Was he “into” me? If he was not, he did a pretty damn good job disguising it for almost 7 months. And if I didn’t “click” with someone and dumped them because of that, I wouldn’t be on his Facebook page every day or leaving a flirty comment on his photo or trying to maintain some level of contact with him, as he has with me. I’d be done with him.

I think he does like you, but that he somehow feels out of it. He feels he’s not really appropriate for you. He’s not sure he could be with someone, again. He’s gotten set in his ways, he believes. He’s afraid of what living together would mean, practically and psychically. He’s very unsure of himself in this way.

I think he is thinking about you. Wanting you. But not wanting to commit to you. Not feeling able to promise you he can make it work. Which, of course, he can’t, and I don’t know why men often feel like we must promise that to women. What do we feel promising to try isn’t enough? Maybe it isn’t?

So if he can’t promise himself to you, then, logically, he has to pull back from you, so you can have a chance with someone who could give themselves to you.

I think you need to have a very frank conversation about what each of you wants, and what it looks like. You have to say your truth, even if it isn’t what the other person wants. Only in this way can you see if there is room to negotiate something you can both handle.

Do you need to live together?
Do you need to be exclusive?
If you live together, what do you want it to be like?
Do you want children?
Could he start right away, if you decide you want them?
What is your financial situation?
Would you separate finances?

and on and on. You could ask a question about the kinds of things you’d need to sort through.

Then you talk to each other. Openly. Just to see if it could work. Right now, he’s made that choice for you without even asking you. That’s not really gentlemanly, even if he thinks he is trying to do what is best for you. You get a say in that.

You have to get these kinds of expectations out on the table.

How will you make decisions? Does he get to make decisions for you without discussing them with you? Will he even recognize when he is doing so? Can he stop trying to think about what is best for you and let you do that thinking?

See what I mean?

Good commentary, wundayatta. No, I definitely do not want children. He has three grown children, ranging in ages from 24 to 29. I’ve met all three of them and had dinner with all of them several times and liked them. They seemed to like me. In fact, his oldest son’s girlfriend was baffled when she found out we weren’t together anymore. She said, “We thought you were perfect for him.”

He had talked generally about keeping finances separate, and I like that, too. That was an issue of contention with my first husband, who thought all finances between spouses should be joint.

This is kind of besides the point, but to me, when I see a young woman with a guy who’s way older, I think to myself, “Maybe this is sexy now when she is 40 and he is 60 (or whatever) but when she’s 65 and he’s 85 and she has to diaper him, or he’s old and infirm and she may still want to go out and travel and enjoy herself, she may be sorry.” I have seen this happen a lot, where some woman marries a guy who’s way older, for money or for love or for both, or whatever, and then he gets old and infirm and she’s stuck and wants to still go out, travel, and she’s stuck with him needing care at home. Something to think about.

@jca My partner is 17 years my junior, I hope not!

Yeah, that may be the case for some people, but not all. I know of lots of exceptions. For instance, his dad is exactly 85, and his mom is 80. They are still very active. In fact, his dad, who was a doctor, retired from his private practice but didn’t want to sit at home all day, so he has a full-time job overseeing interns and residents at the local hospital. My mom, who is 80, is on the go constantly. And my ex-husband, who was 26 years my senior, and is now 65, has always been hyperactive. When we traveled together, even up to the last few years of our marriage, I often tired out before him, and I’m in my 30’s!

@femmefatale Good for you, with all the laws and rules of society and what people say and think, you are not ageist. Love comes in all shapes and forms and ages! I wish you luck and love!

Interesting update. So Friday night I went out on a first date with a guy, this time my own age. (Didn’t really click with him. I just LIKE older men, I guess. Plus, this guy was a bit uptight and is still a student at in his late 30s without a regular job: a dealbreaker for me.)

Anyway, we went to a local bar/music venue. When we first arrived, there weren’t many people there, but when it got closer to time for the band to start, the place began to fill up. I had my back to the door. My ex must have come in after we arrived. We were sitting at the corner, and I don’t think my ex knew I was on a date with this guy.

My ex came up to me, put his hand on the small of my back, and said, “Hey, how are you?”

I said, “I’m fine. How are you?”

He said, “Fine.” Then I think he realized after the fact that I was on a date, and he kinda slunk away. For the remainder of the time, he stood back behind us in the crowd, almost as if he had positioned himself so he could see us. He wasn’t with anyone. When I turned to the side to watch the band, I could see him from my peripheral vision. I had to pass right by him once going to the bathroom.

“Of all the gin joints, in all the towns, in all the world, [he] walks into mine.” Why did he even have to come up to me???

@femmefatale What do you think? Does he still like you? Does he still want you? And what about you? Do you still want him?

This would be funny if it weren’t so sad.

Yes, I still have feelings for him. If he were truly interested, I’d give him another chance—with stipulations. I just don’t know what his intentions are, and if there is definitely mutual interest, I don’t want to push him away. I’m afraid that will happen if I look too eager.

Some have said if he wants me back, he will pursue me. I don’t know. I think if he does/has decided he wants something more, there may be a pride/fear/insecurity issue, based on my experience with him.

After he responded to my FB messages thanking him for the breakfasts he made for me when we were together (which I sent before we saw each other at the bar this weekend), I replied to his last message about enjoying those breakfasts, telling him I missed conversation with a like-minded individual. And the sex. Probably shouldn’t have said that, but I did.

Then late Sunday night, after he had seen me at the bar with the other guy, he replied to my last FB message. He said, “I, too, miss the conversation…and the sex.”

Well, I think it makes sense to play it slowly and carefully. It’s like getting together the first time, only different.

Please let us know how things turn out. Thanks.

JCA
The Update Lady

Will do.

So this week he has been texting me and sent me 2 multiple paragraph messages on Facebook. After the first one, in which he said he has been trying to figure out why his defense mechanisms caused him to feel like he need to bail, I sent him one back saying I didn’t want to be just a frivolous electronic friend, and if he didn’t make up his mind on what he wanted, I was going to extricate him from my life completely.

In the second multiple paragraph message, he said he knows it’s his fault we haven’t sat down and talked in person and we need to find a time to do that. He said, “If I hadn’t been thinking about you, I wouldn’t be writing this.” He also said, “If I complimented you on fb, I wasn’t being insincere or pandering to you. The things I said were my true reactions.”

Maybe I’ll give him another chance… Will post an update.

We have been back together since Election Night. It has been wonderful! He was afraid I thought of him as just a fling and was afraid of letting go, that he might get his heart broken. He said he thought of me every day when we were apart and I took a piece of his soul. The first couple of times we were together again, he was very emotional and cried. He said he finally had to break down and give in to his feelings about me. Things are even better than before. Let’s hope they stay that way. December 23 will be a year since we first got together.

Sounds promising. Thanks for the update. Good luck.