A
female
age
51-59,
anonymous
writes:I went out with someone and I wasn't sure if it was a date or just friends. Partly this is because his whole manner is very formal and polite - although now and again he surprises me by doing things like swearing or he breaks through the politeness by just being very warm and caring as a person. He is 54, I am only just 50. He is my former boss and we've known each other for 10 years and I very recently left where he still works.I asked him out because I wanted to thank him for his help with a project I'd been working on - he really supported this way beyond the call of duty. I know he wanted to start something up with me before, but he has an extremely strong sense of duty and I know subsequently that he was really struggling with being my boss and being attracted to me and he knows that he did flirt with me and, although I like him, it confused me, so he stopped being flirty but remained caring and warm. I had a really awful time with an ex and haven't dated for years. He knows about my ex but not about whether I am dating anyone or not. I know I am insecure, but I also really, really like him. The problem I have is every time I start to relax and think everything is fine, I will read something on the internet that throws me off balance. I can't figure out if the stuff I read is feeding my own insecurities and this is what's stopping me from thinking he will contact me again, or whether he is formal and insecure too and it's possible that I haven't given him clear signals that I like him, so he is playing it safe and being cautious.Good signs (I think) are:I actually let the invitation slide as I thought he was slightly vague about accepting (probably me being insecure even then) but HE then initiated meeting up - when he did so, it was me, not him, who re-instated my offer of lunch.He chose dinner instead of lunch or drinks.He looked really pleased to see me and kissed me on both cheeks.Dinner was fine - lots of talking and laughing, nothing weird happened at all.He asked if I wanted dessert and then asked if I wanted to share a dessert (We did, but using separate cutlery)When he saw my leftover food, he asked if he could try it (I said yes) and used my cutlery to do so (!)He was really quite 'confessional' / opened up about lots of things (but not in any remotely needy or gossipy way, just in a really nice way - this included telling me about some of his personal insecurities - but, again, not in a needy way, more like a self-deprecating way)He suggested we go on for a drink after dinner (we did)There was lots of laughter and lots of reciprocal questioning about each other's lives.Barely any awkward moments or silences - a couple of very slight (like 10 second) lulls. With that said, this was the first time we'd been out together socially when we were no longer colleagues, so it was a bit unfamiliar territory, so to speak.He told me that I look years and years younger than my age, and he really looked at me and smiled a lot (not lecherously, just really genuinely) when he said this.Bad signs (maybe, I'm not sure):He let me pay (though he offered a contribution) - now, this one, technically I don't mind because he knows I'm a feminist and we've discussed money and relationships before, in the context of work, and it was me who offered to take him out to thank him. I honestly don't mind about the money. But what I've read on the internet is that he won't think it's a date if he doesn't pay.He didn't ask me out again, or mention anything to do with the future that might involve me in it.I ended the date after he'd finished his drink - I'd read it's best to do this, but he may have taken this as a sign of disinterest.When we parted to catch separate trains he kissed me on both cheeks again, smiled really warmly and said "keep in touch". Now, initially, because of how he said it, I thought 'great', but then I thought 'hang on, that's what you say when you're not expecting to see someone very often'. I went home and looked on the internet and a lot of people say it IS that someone doesn't expect to see you often - but other people said, no, it can be a sign that someone really does want you to keep in touch but it really does depend on the context.I worked myself into a state, of complete confusion, thinking I wasn't going to hear from him. A friend said I was being overly-critical and the signs were more good than bad and that he knows not to push things in case he is over-stepping the mark. If he hadn't said the last thing he said, I'd have been more hopefulNot the next day, but the afternoon of the day after ie. roughly 36 hours later, he texted me and said "thanks so much for dinner" and he wished me good luck with the preparation for another important project/ public event that he knows I've been working towards and that he will be invited to see the results of. But he didn't ask me out or mention anything like that.My friend said this was a good sign - if he didn't like me he wouldn't have texted at all - and I should text back saying that I really enjoyed seeing him and to indicate CLEARLY that I'd like to meet up again - because if I don't then he won't know for sure. She knows me well and thinks I've not been giving him enough signs that I really like him as more than an ex-boss. She says the 'good luck' thing is NOT some vague good luck with the future kind of 'goodbye' but is different because it's about a specific project he knows about and he will be expecting to be invited to the outcome and he is just being supportive and caring. She managed to convince me.So, I texted back saying how much I enjoyed spending time with him and that if he fancied meeting up again sometime I'd like to hear more about his interest in ...(and I mentioned this hobby / thing that he is really interested in and that he was discussing on the night).I felt fine but then my insecurities kicked in again and now I'm thinking that what I read on the internet may be correct and that maybe what he said when we parted and maybe the text to thank me were simply polite messages effectively saying 'goodbye and good luck'. My friend says, no, he is just being cautious and not over-stepping the mark, and all his other behaviour indicates he really likes me but whenever he uses language his formal training kicks in. She thinks his behaviour during the evening indicates he really would like more than just friendship and that it is up to ME to make this clear and then he will initiate after that.Now that I have made it clear, I feel really vulnerable. I am now worried I will have appeared too keen !! I am worried overall that he is just not initiating - my friend says he is 'prompting' and doing mini-initiations and I'm worrying too much.
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Fancy yourself as an agony aunt? Add your answer to this question! A
female
reader, anonymous, writes (26 February 2018): Thank you Malvern. I do see your point. I honestly freely admit - and i have admitted here very openly, that I am insecure. I know why this is and I try really hard to overcome it but it tends to creep up on me. I think what has happened - and what you are picking up on - is that I myself may have rushed to an extreme because him not being more forthcoming and seeming to 'shut the door' on my very gentle advances has triggered my own fears of rejection / abandonment. I feel like I will never see him again, but that's not what he is saying is it? I have thought about him a lot today - not just in terms of what I want (in a more selfish sense) from him, but just him, in his own right and what he might be going through and needs for himself. There were other things he said and did which indicates to me he is possibly going through a bit of a mid-life crisis and, in particular, he is finding it hard to come to terms with ageing. He has said many, many times before now, that he feels 'old' - it is always in a sweet, self-deprecating way, but there is an undertone to it. He also got told off at work recently for having a 'combative' approach to a client when this was not necessary - I think he is quite angry and frustrated with his life overall, despite being a sweetie too. I know he is really struggling with his own sense of where his career is headed and what the next phase of his life may be, and bringing up a teenage son to boot. It may well be that he felt that helping me with my very difficult project became part of a much larger struggle that he himself is going through, and whilst he chose to get involved in helping me, he now needs to know that he can also get distance from that without being 'punished' for just needing space. I don't know him well enough on a personal level to be able to say to him "I really care about you and I feel for what you may be going through" and I also sense that nothing that any woman could say, right now, would help - and may even make him feel less manly than he perhaps does.So, in short, I think his possible 'mid-life crisis' is triggering my 'fears of abandonment'. I need to get a grip and stop seeing this as some major tragedy, take myself less seriously and just enjoy life, and I think the best thing I can offer him is space to make his own decisions in, whilst letting him know that I care for him and he can use my cutlery any time..!In short, you are right - I just need to calm down and chill and separate off what's happening in the here and now of adult life from things that happened to me years and years ago. We will see.Thanks so much for your input, it honestly does help, I am so out of practice with dating and so on, that I've been a bit lost with it all.
A
female
reader, malvern + ♥, writes (26 February 2018):
 I'm not quite sure why you're making such a big issue of all this. He is clearly interested in you otherwise he wouldn't contact you or arrange to meet you. There are a lot of men who don't like to rush into things and he's one of them. He's taking his time, he's weighing up the situation, he doesn't want to rush in and make a fool of himself. Be patient ! I once went out with somebody at the same age as you are now ,and he wouldn't kiss me for the first three months ! He later told me he wanted to be sure. Better that than some octopus of a man with his hands all over you. Your man is worth waiting for, so just sit back and wait for the situation to change !
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A
female
reader, anonymous, writes (25 February 2018): Thank you Male Reader Anonymous, for taking the time to write.
I think I went into so much detail because I was afraid of 'fooling myself' into believing something may happen when it might not.
I was trying to be neutral / unbiased, in assessing what went on, knowing also that I am insecure.
As it turns out, since I wrote the original post and had the responses to it, he did respond to my text message. He totally ignored the part of my message where I made it as clear as I could - without seeming desperate - that I really enjoyed his company and would love to hear more about his hobby. He only very briefly replied to some other information / idea I had offered to try to help him. Then he told me to "take care".
Like both of you who responded, I honestly thought the level of intimacy, from him to me, meant something more than just a casual friendship where you don't really expect to see the person again, if at all.
Seems I was wrong. Trying not to be heart-broken, but it's a tough call. And makes it difficult to feel confident about 'reading' any signs given by any other man in future.
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A
male
reader, anonymous, writes (24 February 2018): Dear Poster, sorry to say half way I stopped reading your very long post because I could see that you care a lot for the Gentleman in question otherwise you you wouldn't have caught every small detail of your friendship as you did, and certainly he cares a lot for you too considering he ate your leftovers using your cutlery. Lol I haven't done that even with my wife. You are two mature people you should be able to decide what you want. What can we advise you? Ok maybe we become more hesitant as we grow older but I think all the signs are there. You care a lot for each other.
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A
female
reader, anonymous, writes (24 February 2018): Dear Youcannotbeserious
Thanks so much for this, I honestly really appreciate it. My gut feeling is that he is really afraid and is equally afraid of hurting me - I think you are right, that we are 'circling'. Although he's not obviously initiating, I still think he is creating a 'safe space' 'safe boundaries' and taking things slow, in case something does happen. If anything, I am concerned my own insecurities will sabotage everything-probably it's this that i need to work on!! I will really take your advice to heart and remember this when I feel insecure. Thank you again for this, it helps a lot.
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A
female
reader, Youcannotbeserious + ♥, writes (24 February 2018):
 Sweetheart, for crying out loud, listen to your friend (who you admit knows you well and who appears to talk a lot of sense) and STOP READING RUBBISH WRITTEN ON THE INTERNET BY RANDOM STRANGERS. These people don't know you, they don't know your ex boss. They are just basing what they write on their own experience. I bet, if you looked harder, you would find completely conflicting opinions on EVERYTHING you have read.
It sounds like both you and this guy are battling many insecurities between you. You are both circling each other with great caution, over-thinking every single little move and word, and worrying what the other is thinking. You really need to stop doing this.
Assuming you are both single (you haven't said differently), you need to relax a bit and stop making such a big deal about every single tiny thing. It sounds like he likes you a lot but, possibly due to the earlier knock-back, is terrified of putting a foot wrong in case he spooks you (just as you are with him). Sooner or later, you are both going to have to take a leap of faith and hope for the best. Fortune favours the brave. Be brave.
Good luck (and I don't mean that in a dismissive way, lol!).
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