I am a man in my mid-40's and met some time ago an old friend (woman, mid-40's as well) when travelling (to her city). I traveled there again a few times (every few months) and it is obvious that a (very positive) sexual tension between us is raising.

I usually have a dinner with her, then we part ways but there is always this untold sadness that it did not go further (on both sides). Long story short, it is extremely likely that we will end at my hotel over one my next travels.

My problem (and hers as well) is that we are very much grown ups but also very much inexperienced in how to deal with the transition between the dinner table at a restaurant and the bed in the hotel.

I would like to make it as "natural" and non-awkward as possible but I honestly do not know how to handle the transition.

To be clear: this is not strictly a dating advice, in the sense that we will be fine during the dinner and (hopefully) fine when in bed - it is really that way in between that is complicated.

Also the fact that we both want it to happen is clear for all kind of reasons.

This will be in a large city, in Europe, the hotel has a restaurant but we will likely have dinner somewhere downtown.

  • How long is the way from the restaurant to the hotel? Is it in walking distance or do you need to take a car? Is a taxi acceptable? – XtremeBaumer Oct 12 at 7:48
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    @XtremeBaumer: it is almost certain that this will be a taxi. It could be a very long walk (~ 45-60 min) - which in other conditions would not be a problem but here it would be too long. – user22510 Oct 12 at 8:20
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    Welcome to Interpersonal Skills! Please don’t write answers in comments. It bypasses our quality measures by not having voting (both up and down) available on comments, as well as having other problems detailed on meta. Comments are for clarifying and improving the question; please don’t use them for other purposes. – Tinkeringbell Oct 12 at 18:27
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    *I usually have a dinner with her, then we part ways * > With regards to this answer, does that mean that you part ways at the restaurant? Or is there e.g. a cab ride to the hotel and do you part there to each go to your own room? (I've left a comment that goes for the first, if I'm wrong, please correct me :) ) – Tinkeringbell Oct 12 at 18:58
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    I think a country tag would be very relevant to this question. – Radu Murzea Oct 16 at 6:55

12 Answers 12

up vote 71 down vote accepted

As @JCJ suggests, it's unlikely you will eliminate the awkwardness entirely. But one thing you can do is prepare a flimsy reason to invite her to your hotel. For example, "want to get a bottle of wine and drink it in my hotel room?" Most likely, she'll understand what you're really asking, and then the cat will be out of the bag (whether or not either of you acknowledges it verbally). If she accepts the invitation but misses the subtext, that's fine too--you'll have solved the problem of getting to the hotel, and escalation should be easy from there, if she's as interested in you as you say. (Needless to say, you should make sure she's comfortable at every stage of the process, and if she's not, de-escalate things politely.)

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    You might also mention that it's become a trope in television and movies that at the end of a date when one is walking the other back to their place, if the other says "would you like to come in for some coffee/tea?" it's almost always a sign that they're looking for something more. (can't find the TV tropes link at the moment) – scohe001 Oct 12 at 15:14
  • Comments are not for extended discussion; this conversation has been moved to chat. – Em C Oct 15 at 22:37

From personal experiences, it's always going to be sort of awkward, because very few can act like a suave George Clooney-esque character from a movie, so just embrace the awkwardness and have fun with it. Even in movies they usually cut from the bar lounge to the bedroom. Hell, even living with a significant other for 10+ years and moving from the living room to the bedroom is still awkward in the sense that it's just like "uh let's go to the bedroom", rather than something from a steamy novel or whatever.

You most likely won't be able to make a smooth transition from a restaurant to a hotel room, but it can be made fun by being happy about the situation, giggling, initiating some light intimate contacts etc on your way there.

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    This doesn't completely answer the question in my opinion. The OP's question isn't only about how to make it not awkward but more importantly how to make it happen at all. Since he failed to get with her to the bedroom entirely. – Ivo Beckers Oct 14 at 11:54
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    @IvoBeckers OP is looking for a non-awkward method, while this answer indicates there is none. The first step of fixing a problem is identifying the problem. – Mast Oct 14 at 17:48
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    "living with an significant other of 10+ years". Should that be "for" or is your SO not particularly old ? – Evargalo Oct 15 at 14:45
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    @Evargalo - Not necessarily. "living with an SO of 10+ years" means they've been involved for 10+ years, but they might have just moved in last week. "Living with an SO for 10+ years" means they've been living together that long, but they may have been involved for many years before moving in together. They are not equivalent statements. – Dave Sherohman Oct 16 at 8:10
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    @DaveSherohman : thank you, it makes sense. My (lack of) understanding of English still let me regularly miss such subtilities... – Evargalo Oct 16 at 8:21

When the bill comes at dinner, tell her that you've had a lovely time spending the evening with her, that you wish the conversation didn't have end, and that also, you would be overjoyed to be privileged enough to continue to spend time with her the remainder of the night. If she is on the same page, she may suggest that the night need not end now. Then you offer to share a cab back to your hotel room so that you can keep the conversation going.

Making a reference to coffee is unwise and unneeded at this point as it directly implies sex; you should allow things to go that direction naturally as opposed to forcing the issue. In my opinion, women generally do not appreciate the assumption that sex is expected, even if they are attracted to you; and to be clear you should not be expecting anything.

The next part of the transition need not be overly awkward, but rather a part of foreplay. That is to say, on the taxi ride to the hotel, if she consents, try kissing her. Start on the lips, then slowly move up and down her neck.

Another thing you could try, would be to, if she consents, hold her hand; however, this might be a bit trickier. Some people will not feel comfortable with this if they don't see the possibility of a long-term romantic relationship. But this approach might be more acceptable to you if you are not comfortable with PDA. Another variation of this would be to gently rub the fingers of your spare hand up and down her arm.

Light affection such as the above, will not only reduce awkwardness, but also may make the overall encounter much more enjoyable for her as well.

Have fun, just make sure you are both on the same page!

I don't think that it is possible to make a completely non-awkward transition from the dinner table to the bedroom if the sole purpose is sex. Of course, you can make it less so, by applying humour and both being able to laugh about the situation. This is something I often do and helped me in general in awkward situations.

My advice albeit would be to not only set the goal to sex but set the goal to a cozy evening together, maybe watch a movie you talked about etc. If everything goes well, you understand each other and have fun, lying in bed, most certainly cuddling will automatically lead to intercourse in most cases (if no one is super shy and both don't like taking the first step).

Advice:

So my advice would be to rather than for sex, meet up afterwards for an occupation you both like, aka watching a movie, and you will see what happens. This IMHO is way less "awkward" because you can talk about topics like the movie, or other things while no being so nervous as "what should I do next" because during a movie you have loads of time to go step by step.

EDIT:

If you are unsure how to set up the transition you might ask when the dinner is concluding: "As you are also fan of X would you care to watch X together at my room i rented for my stay here? :)"

If there is attraction on both sides this is a no brainer :D Actually thats exactly the way i got together with my current girlfriend after a very very extended coffee. In our case it was Harry Potter ;D

Many years ago, a partner and I (still extremely good friends), used to have fun playing the hell out of this aspect of an evening. Typical conversation:

  • "Can we have sex yet?"
  • "Nooo! You've got to invite me in for coffee!"
  • "Okay. Would you like to come back to my place for coffee then?"
  • "Of course!" (Arrive, door opens, door closes, coffee brewed)
  • "Okay, done making coffee, can we do sex now?"
  • Nooo! You have to tell me you love me, and make me feel special!"
  • "Is it okay to lie?"
  • "Maybe?"
  • "Okay. I love you, you're special, and now can we do the bed thing?"
  • "Noo... I have to resist, it says so in allll the movies... (etc etc)"

I know this isn't quite the situation you're in, but laugh, love and enjoy, and maybe this will give you a smile, and some ideas!

The awkwardness is there to fill a space the same way that there is awkward silence when a conversation stops and nobody knows what to say just then.

To remove or avoid the awkwardness, do not leave an empty space. Instead of going from dinner to sex, make the transition smoother with more steps. Pick your places at the dinner so that you can start with light, playful touches. Then go for a walk or some other activity where more touching is possible. The walk can "coincidentally" lead towards the hotel. Touching becomes kissing, kissing becomes more sexual touching, and this you can easily continue well into the room.

Plus it's more fun this way.

Don't see the space between dinner and bed as awkward. See it as foreplay.

For what it is worth as another 40 year old but NOT in the scene, I'd really simply suggest the honest approach. If you feel there is 'sexual tension', the 'hard to get' game isn't so fun.

I may have missed this, but is she local with a house/kids? Reasons not to go that way?

You could say during the last 15 minutes of dinner, ordering dessert, simply- "I'd really like to get dessert but there's nothing here that strikes my fancy. Do you know anywhere else?" That opens up the option for her to invite.

You could also say "I really don't want the evening to end, but I understand you've got to get to work tomorrow. If you don't think you'd be too tired tomorrow, would you like to get a bottle of (beverage) and watch some sort of lousy movie at my hotel? I guarantee it'll be at least 4 years old and with very bad special effects"

OK, more my style on the last one. And you've provided multiple ways for her to say NO without hurting your feelings or implying she owes anything to you.

And you've got to seriously consider that she can say 'no' (And so can you!) at any point. There's nothing that's owed at any point. Even "I really love seeing you on my trips, and would just love to spend more time with you somehow". (careful using the L-word, ya know?).

Good luck. I wish you well and hope that you can find happiness- and that she can too.

It could help to suggest going back to either person's place before dinner ends. If dinner is one hour, then say 15-20 minutes before, you say something a bit more refined than

"Don't let me forget, but I also want to tell you (more) about topic N. I have this-food and that-drink at my place. When we finish dinner we can head there, but for now let's continue with topic K. You were saying ..."

If you are interrupted with a strong objection (not a question) to where you two will go next, then that's a no. Questions are not objections. So don't flake or get timid if asked stuff like "how far away are you", or something teasing like "is that the best place to discuss it".

Then you continue with topic K. Dinner ends: "Let's get a cab/ride-share back for this-food/that-drink." Add a line about it, like "I first had this in..." "can you believe it costs less than the water they leave for you on the counter?"

All the awkwardness comes from waiting until the end to suggest the next location. You suggest mid to 2/3 through the first location, and reference it a 2nd or 3rd time when things end.

Also, it is absolutely OKAY for you so EXPECT sex at some point during the night. The same way I can expect a 6 on the next roll of a dice. It's just and expectation, and there is a 6 on the dice.

It's not okay to act inappropriately should the reality not line up with your expectations at some point during the night. I hope that makes sense. (Too many people saying not to expect it. Could the expectation mess with how you interact with her? Yes. It it wrong for you to expect it - i.e. should you not be allowed to think whatever you want? No. Think what you will).

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    Hi VISQL, I have a question about your answer. You say it's normal to expect sex at some point in the night, but I'm not sure I get what you're saying then. Do you mean it's normal to think they're likely to want to have sex, but that it's ok if one of them doesn't (anymore)? As this is a sensitive topic, I just wanna make sure your advice takes into account mutual consent. Would you mind enlightening me about this? – avazula Oct 13 at 10:27
  • You are free to expect what you want. You may be wrong, or right - as you are predicting a future event. If sex is what you expect, then you will act to facilitate that outcome. The actions are what you must pay attention to. You don't necessarily have to feel bad about the expectation. – VISQL Oct 14 at 16:58
  • I got that, indeed. However, even though I agree with you, I think it's important to remind people that even if you expect something sexually related and thefore will act in order to provoke what you want to happen, you should push if you see that the other doesn't want to do it (anymore). – avazula Oct 14 at 18:57

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.

I'm probably late to the party here, but i'll give you my view on this, which isn't really an answer but depending on how you take it, it might be for you.

In my personal experience and my development through teenage years into adulthood, i went from having 0 sucess with women to having alot of it. Awkwardness was a HUGE battle as i was a bit awkward in this transition. What I figured out was that awkwardness is a choice. It's your choice to define a situation as awkward and trust me, once you do, it is. If you never feel awkward you tend to influence the people around you to feel the same as you, ofc this goes both ways so as soon as you feel awkward she also feels, at least, that you are making things awkward.

It's not about the exact situation or what was said and done, it's about how you and her react to these things. Ofc this is what confidence is called, being on top of the situation w.e. happens and never letting things get awkward. But what i'm trying to get across with my answer is that awkwardness is contagious and you are in control of it.

With that said, i understand it doesn't quite answer your question and it's just my personal experience and not fact. I hope it can help you in the future tho :)

Ps: sorry for any typos, not primary language and writing a bit fast as i'm short on time!

Among the other answers I haven't seen the obvious thing:

Make an open and honest proposition. At some time, maybe after some nice exchange over the desert, tell her that you enjoy her company so much and you feel for her so much and you have been sad every time when you parted ways the other times you spent together. Tell her exactly what it is you feel: You would like to invite her to spend the night together.

That will still be awkward to some degree, mostly because there is a looming possibility that you misread her and she'll be surprised and taken aback and say no.

To deal with that awkwardness you could make it explicit as well, starting with: "You know, I feel like on my first date but there is something I really have been wanting to tell you for a while ...". If she's on the same page she'll be touched because you are actually blushing and you are sincere and you dared. Chances are she'll say "I thought you'd never ask."

Being sincere and honest is a good start into a relationship which is why I would not try to be manipulative or clever about it.

Good luck :-).

Use a proposition to take things further, which is obviously exactly that veiled as something else. This eliminates what is called "mutual knowledge" and allows unspoken subjects to easily be discussed in code without causing awkwardness. For example early in dinner you might tell her about the lovely decor in your room, or the new suitcase you have or whatever. You can mention that it really has to be seen in person to be appreciated. The less special it really is, e.g. you need some help with the squeaky doorhandle, or even if it's something you can joke about, the better. When you get there... Oh look the squeaky doorhandle seems to have fixed itself, she must have a talent... What other talents does she have... It doesn't matter really, as long as your intention is clear but is something that opens the door for her to go up if she wants to, and leaves you with the ability to save face and pretend you meant nothing by it.

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