As this is more like answer to OP and others, than just comment to @VISQL / @avazula :
I will put it a little bluntly (sorry):
OP say, that he regullary meeats his friend at dinner (every few months or so) and that they enjoy it and that his wish is to end in bed with her sometime in future, and he feels, that it may be possible (so she may feel like that too), but it is AWKWARD to make steps from dinner to bed.
They both are adults, they respect each other and are friends. It is really possible, that it may result in the bed - would not be first or last time in world.
The pure fast, that she meets him on dinner each time possible and they both enjoy the time and are sad, when it ends suggest, that there may be more, if situation will came right way.
So I read VISQL comment in the way, that OP SHOULD expect, it will happen and so BE PREPARED for it (that means not run away in panic, if they happens one night in his hotel room in romantic mood). He does not say to FORCE her into it against her will, but he say to keep in mind, that it is possible (and desired) result and that OP should be positivly thinking toward it. (If I expect, that I MAY end in hotel room with my friend, I would make sure the room is tidy, there are like two wine glases and wine bottle somwhere, as well as there are two cups and coffie maker with coffie and suggar ready, also some chips or something like that, BEFORE I leave the room for dinner (and also be sure, that I have condom or two, just in case, but not in clean display). (If my expectation came true, then it would help, if not, it does not hurt.)
On the dinner I would keep in mind, that I want this nice end and I expect it to eventually happen. So I would invite her over the dinner to (say) see movie with me in sure way and with positive thinking about that, like " ... BTW I got recently this movie I enojeyd it and was thinking, you would also enjoy it, so I took it with me, would you like to see it with mee today?" (expecting her to say something like "hmm, why not" or so and take it as yes. Also if the reaply is "Shoud I do it? Would not be that inapropriate?" I would say "Yes, sure you should. I would be really glad, if you do." - but if she say "Sorry, I cannot today I have to go there and there and ... and ..." then I would reply like "Ok, maybe next time?" (maybe she really does not so much time today) and finish the dinner happy as usual and offer it next time too. But if she say "Sorry, I am happyly maried, I would feel that like cheating" or "Sorry, I do not want to go that far", then I would say "Oh, no problem, anyway, I like to have dinners with you and talk about so much things" and left it be as it is)
Yes, if she take all my offers positively and we end in bed and are happy next morning, it is like the expected 6 on a dice - does not happen each time, but MAY happen. And all went well as I expected. If she turn it down for today, it like 4-5 on a dice, happens, no reason to expect I will get 6 next time I try. If she turn it down totally, its like 1-3 on dice, not what I hoped for, but if I take it right, we will be still friends, who does to "just dinner" every few months.
On the other hand if I would expect, that there is no way for positive result (I would even not try at all, but if I would), that it would sound more like "I have that movie on my room, but I suppose, you will not go with me to hotel anyway" (and she will turn it down for sure - or nearly for sure, depends, how much she wants that result). So better EXPECT the best, but be not discouraged if not everything will go the best possible way. Just avoid the worst way and be nice and fair all time.
Also try to think about how it looks from other side - she meets you regullary, she feels good with you, but she is not the one, who should offer spending night together - you are not Prince on White Horse and she is not 16 anymore to faint, if you just smile on her - so the common sense is, that you would say her nice words, you would suggest to do next small step, then another, until you are there, where you want to be, while she is expected to accept it, if she is comfort with it, or even "little defend, but not so much, that she would succeed with defence" to make her more valuable price and "not so easy to get" - its a game and while you both enjoy playing, it is ok to play it. If she would like to stop, if would be told in different tone ("I am not sure, if I should accept such invitation"/"Yes, such beautiful lady really should do"/"You talked me into it" versus "Sorry, I do not want to"/"Sorry, did not want to press you"/"Anyway, will we have dinner again next time?"/"Yes, we will")
Any way, if it goes well, you are expected to do a lot of "small steps", each little far, then previous and let her decide, if she want to accept it, or stop it just there. You can bet, she takes care about her, she knows it, you know it, it is common sense for mature woman to dress good, have some nice earings/bracelet/parfume/clothes/shoes/whatever, when she goes to dinner with old friend. But still it is good to compliment her on that, on dinner about bigger visuals (that color really suits you and makes you hair even more beautiful), in cab, when you sit near each other, than in restaurant (you smell really sweet), in the hole room (yous skin is so soft and warm) - yes she knows, but it makes her happy anyway - and it is true, so nothing to be ashamed to say.
You tell her about the video in course of dinner, let her some time and ask here to go see it near the end of dinner (if she react immediately like "I would like to see it" - if basically mean "I just want you to make me offers for each next step, so I can agree, as I cannot say it beforehand, just ask me and let me to say YES"), talk about it and about her in the cab, offer her some wine/coffe, run the video, put the chips in bowel and sit near her to share it, then touch her, put hand around shouldes, touch her hends and more ... still expect, that if she went so far, she would go even another step, until she say to stop. If she does, then stop (ofcourse), but then you know, that next time you can safely go so far and maybe one or more steps too. It is not problem, if she is not ready continue today, maybe next time. But expect, that she would like to continue, until she state otherwise, as it is you, who should do these steps.
Your intent to sleep with here is like 100% (if she would agree), but there is a lot of awkwardness around the way. It is possible, that just now her intent to sleep with you is also high, but the awkwardness totally stops her, from saying so. But she may agree to do a lot of small steps, with are not so awkward and could be seen as logical, you just present them as "totally normal for adults as us" and she is required to not reject it (it is much much easier, that to initiate it).
Imagine, what would happen with awkwardness, if she would next time invite you for a little walk, then some hot tea at her home, run some movie, while talking about something else, then put out two glases and bottle of wine on table and sit near you, just sipping the wine, head on your shoulder, looking at the movie. And on titles she would excuse herself, went in bathroom, return in towel and offer you to use the bathroom too. Where it would end. And how muchj it would be awkward to you to "just agree" with each of these steps, if presented like something "normal and expected".
(Yes, would be little awkward, but not so much and I bet, you would just follow, even if you would on the start on dinner had intent only like 30% to sleep with her - it there would be no contradiction.)
So this is, what I think, that VISQL meant with EXPECT the positive result as you would EXPECT 6 on the dice you just throw. It may happen, it may not, be cool, if it does not happen, but EXPECTING it you make it more probably to happen it and lot less awkward at all.