I can send him admiration, do you think it will be odd? We haven't said much to each other in the last 5 months.

10 Creative Questions To Break The Ice And Get Them Talking
1. If money were no object, what kind of car would you drive?
Very nearly everyone drives... and very nearly everyone has thought about what their "dream car" would be. This question lets you find out a little bit about them (what kind of car they like) and gets them talking. You can continue by asking why, or possibly going to what kind of car they would never buy.

Alternatives: Almost anything works here, just start with "If money were no object, what kind of blank would you get?"

2. What's the strangest thing you've seen?
Here's a chance to get them talking and laughing... and getting someone laughing is an easy way to lower their walls. This question works particularly well if you have a truly bizarre story of your own to tell.

Alternatives: Replace strangest with any other - est... it could be biggest, loudest, etc.

3. What's the best restaurant you've ever been to?
This is a good way to find out what kind of food they like, if you're thinking about asking them out at some point. It also might give you an idea of a good place to eat, whether or not it's with the person you're talking to at the moment.

Alternatives: You can substitute other things for restaurant, but most things have less general appeal, and the ones that don't are usually asked all the time. This is one where if you want to change it, you'll have to base it on the particular person you're talking to at the moment.

4. Where is the most exotic place you've ever been?
This is a chance for them to open up and tell a story... and that lowers their walls. If you've been to the same place, you've got huge bonus points... shared experiences are the fastest way to get closer to someone.

Alternatives: Most exotic can be replaced with farthest, most dangerous, etc.

5. What is the biggest event, by number of people, that you have seen in person?
Another chance for them to tell a story, and another chance for you to have similar experiences. One warning, though... don't ask questions like this and always have a bigger, better story to tell... even if you really do, it will make them feel small.

Alternatives: Replace biggest with something like most expensive.

6. What is the dumbest thing you've ever seen someone do?
People almost invariably like to tell stories aboutthe dumb things they've seen, particularly when it was someone else that did it. If you're really lucky, the person might tell you about the dumbest thing they have done... you can lead the conversation in this direction by telling them the dumbest thing you've done after they tell their story about someone else.

Alternatives: Really you can replace dumbest with nearly anything... nicest, weirdest, most spectacular, most dangerous, etc. Very little gets someone to really go off like dumbest, though.

7. What is the most expensive single item you've ever bought?
You might want to add words to exclude houses and cars, it's up to you... this question gives you an idea of what the person thinks is worth paying extra for, what is important to them. That can be amazingly valuable both to continue the conversation right then, and in any future times you meet.

Alternatives: What purchase did you regret the most is a related question that can be interesting... but it may bring up bad memories, and that's not really what you want when you're breaking the ice. You might go for the most fun purchase.

8. What is worst tasting thing you've ever eaten?
This is another thing that people usually remember quite clearly and don't mind sharing. It can even be another shared experience, if you've eaten the same thing... particularly if you also didn't like it.

Alternatives: Most delicious, hottest, most sour... any of the major factors in taste can be used.

9. What is the most vivid/realistic dream you've ever had?
This is one that can also tell you a lot, but it's also more dangerous than most on this list... not everyone is comfortable sharing their dreams If they are, though, this can get you past a lot of walls they might have, moving you pretty much straight to the "friends" level of relationship (and not in the bad way, for those seeking romantic relationships).

Alternatives: You could also ask what movie (or movie character) they most identified with... it's basically probing for a deeper opening up. If you get it, great... if you don't, they may push you farther away than when you started.

10. If you could make all of one kind of thing go away, what would it be?
What would you make go away? It can make you think of a lot of things, and things can come up and be laughed about (think mullets)... this question is very open-ended. If you get together more in the future, it can even be something that you bring up regularly, on the spur of the moment... "Okay, THAT is what I would get rid of".

Alternatives: You can do the positive (and more common) side - If you could only have one kind of blank, what would it be?

Ten examples, with alternatives... there are more than twenty questions listed above that you can use to get someone to open up and start talking. And, since they are unusual, they will make that person far more likely to remember you. After all, how many people have you told the worst food you've eaten?
Being remarkable, in the dictionary sense of being worthy of being talked about, is just about the best thing way to establish a new relationship, whether it's business, friendship, or romantic. It also helps spread your "network" as they tell the people they know about the interesting conversation they had the other day... if you happen to meet those people, they will already know who you are, which means the ice is already half-broken right from the start.
By the way, the worst food I've ever had, that I can remember, is beer cheese. Yes, I should have known... I tasted it anyway, and it was just as bad as it sounds. Maybe worse.

Well bummer he just told DD17 that it's not a good idea for him to sleep on the couch. I think OW is whispering in his ear.

Trying not to be bummed but I guess it's good that I at least put the offer out there.

I know I'm learning to not wear my emotions on my sleeve. It's a good thing and a chance for me to grow and to not be moved by my circumstance.

I would put up new pictures of you and the kids doing things he used to like to do.