How to tell / hint at a guy that you want to take things further?

[rara]

What's the best way to tell a guy you like him and want to see if things can be taken further? I'm pretty reserved and am not sure I could have the courage to say it explicitly. What's the best way? Hint at it? Take a deep breath and blurt something out?

 

The guy in question is a very long standing friend (years), I think he dropped some hints a while back to see how receptive I was to a relationship. At the time I just wanted to remain friends so I shut it down nicely by 'misunderstanding'. He has dropped the topic. But, having thought about it, I've now changed my mind.

 

Given that a) I can't be 100% sure if he was dropping a hint or was just having a weird conversation or b) did want something more and has now changed his mind and c) I'm shy and have never had to do anything like this before, how do I proceed?

 

Sorry for sounding so stupid but I just don't know how to proceed. Drop a major hint so if he refuses, I can back out? I kind of want it to be explicit though, I don't think I could take the uncertainty and be thinking 'did he understand what I meant'. On the other hand because we've known each other so long I would like to preserve some dignity. I also think that the theory of just telling him is good, but in the moment I suspect I'll panic and won't do it. I also worry it may seem a bit weird to be suddenly like 'Oh let's have a relationship'. Oh and he's out of town for quite a while so this will have to be over the phone.

[Gloria25]

For one, is he available?

 

I mean, you don't wanna spill out your guts/heart only to find out he's moved on you know.

 

Since you two are friends, do you hang out? Is he open to hanging out with you?

 

Even if it's been a while, who turns down a coffee - especially with a friend?

 

Just contact him and say you wanna do coffee to catch up, then tell him pretty much what you said here - which is that you believe he was dropping hints of interest, and you wanted to know if he wanted to take things further.

 

BTW, by having the coffee and "catching up" you can probably feel him out and find out how's he been, etc before you ask the big question. Hopefully that way you won't blindly put yourself out there. Oh, and ask him towards the end of you almost finishing your coffee (and him too) that way if he turns you down, you can exit w/o crying or something. You can be like "well, nice catching up with you"...maybe even kiss him on the cheek/forehead and leave gracefully.

 

Now, if he still turns you down - no harm, no foul. I mean every time we put ourself out there, there's some level of risk. If he turns you down, then grieve and call it a day.

[Erised]

I vote be explicit. Uncertainty is no fun.

[Danda]

In this scenario I think you owe it to him to be explicit, because previously you pretended to have a misunderstanding when you thought he was trying to gauge your interest. Friendly newsflash: He's probably not that stupid and is aware he was rejected. And he will probably be thinking about that if you are dropping 'hints'. Best case scenario, I think, would be if he thought you were messing with him, and that's not a very good outcome.

 

If I were you I would actually start by bringing up that time when you thought he was dropping hints, be honest in that you weren't sure and weren't ready, so you played it off as a misunderstanding because you valued the friendship and didn't want it to be hurtful or awkward. Let him know that in the time since then you've been thinking about it and are interested if he was indeed dropping hints back then.

 

The reason this is my advice is because if I took a chance and dropped hints of attraction and got shot down by them pretending to not understand what I was saying, the above approach is about the only way I'd feel okay about trying with them if they changed their mind.

[toscaroscura]

If it were me, I would just be honest. This is assuming you have a good friendship with genuine caring and love behind it. Say that at the time, you weren't in a place for a relationship with him, but now your feelings have grown.

 

And I really suggest doing this in person, even if you have to wait a while. In the meantime, ramp up the affection and contact to him! This is a good opportunity to show him how much you care about him.

[preraph]

Next time you'll be around him, wear something low cut with a good bra.

[Shining One]

Next time you'll be around him, wear something low cut with a good bra.

Then throw the bra at him. He'll get the hint.

 

 

On a more serious note, you'll need to do more than wearing a revealing outfit since you've previously rejected him. You're past the time for a subtle approach.

[shet]

You shut him down before so he'll be cold. Remotely mature men don't ever let feelings resurface on their own under such circumstances. It's on you to reopen the idea for him. You'll have to be direct. Just say it. You'll find it's easier halfway through saying it. Try being subtle over coffee and you'll just annoy him by reopening old wounds, warming over yesterdays hash, seemingly for fun.

[Gloria25]

You shut him down before so he'll be cold. Remotely mature men don't ever let feelings resurface on their own under such circumstances. It's on you to reopen the idea for him. You'll have to be direct. Just say it. You'll find it's easier halfway through saying it. Try being subtle over coffee and you'll just annoy him by reopening old wounds, warming over yesterdays hash, seemingly for fun.

 

I didn't tell her not to be direct...

 

I'm just setting the mood/environment on "how/where" she should tell him.

 

Also, I still think she should find out what his availability is and "feel him out" over the coffee before she does all the direct talk.

 

I mean, really? Is she to "out of the blue" just show up on his doorstep and be like "oh, we need to talk"?

[Jules Dash]

worry it may seem a bit weird to be suddenly like 'Oh let's have a relationship'.

 

I wouldn't get that explicit. Addressing a relationship before a date may be jumping too far. Just ask him out. I think he would bd flattered.

[shet]

I didn't tell her not to be direct...

 

I'm just setting the mood/environment on "how/where" she should tell him.

 

Also, I still think she should find out what his availability is and "feel him out" over the coffee before she does all the direct talk.

 

I mean, really? Is she to "out of the blue" just show up on his doorstep and be like "oh, we need to talk"?

 

Sorry, that wasn't a response to you, just a random example. But while we're here; she's said he's a friend, so it's not out the blue, and she's said she's timid and reserved, so her "feeling out" isn't necessarily going to be subtle or useful. Best sack up and just get to the point for maximum clarity.

[rara]

Thank you for the replies. It's definitely clarified things a bit. So, firstly, we are really good friends and tend to talk about most things, it's just this is different because the stakes are high and I think neither of us wants to get shot down! We have known each other for years and have a very warm relationship. Also, although we started off as friends in a group the others have dropped by the wayside for him - I'm still friends with them but he just decided he didn't want to pursue friendships with them, so when we meet it's just the two of us. And we talk on the phone all the time.

 

Secondly, I'm convinced that it was completely platonic for both of us until maybe 7 to 8 months ago which is when I noticed a slight change in his body language etc. He dropped the hints when we spent the day together a few months ago - he arranged the day out and I think it was for that purpose.

 

I say "I think" he dropped hints because I'm so bad at this kind of thing I can't be 100% certain. Like I said before, he could just have been having a weird conversation without meaning he wanted me to be his girlfriend. Again, I'm so bad at this I need men to bluntly walk up to me and say "I think you're attractive, do you want to go on romantic - as in not as friends- date"! Lol. But the body language seems good, like our arms are constantly touching as we walk down the road etc - and it's certainly not me getting too close to him He's also started picking up the bill which we never did before. He normally does this when I leave the table otherwise I would argue to pay half (as I do with all my friends, male or female.) Although this could also be because he's got a pay rise and feels he can afford dinner for both. All I'm saying is if I've misread the signs that would be so, so embarrassing. What if he's just being a caring friend who wants to confide in me and just be nice by paying? And even if I didn't misread the signs he could have changed his mind. Sigh. Although the last time we met was a couple of weeks ago.

 

Finally, it has to be over the phone because he's been sent to another city for work. And when he does come back it's quite literally for a quick meeting and he's got to get back to the project. I think to have this conversation in person we would have to wait until March at the earliest and I kind of think we are in the moment now, another few months and the moment could be lost for both of us. If I'm honest I'm also a bit paranoid he'll meet someone else, or change his mind (if he hasn't already) thinking that I'm definitely not interested. I hate for it to not happen because he moved on thinking I was not interested.

 

Oh and also, I'm actually not a particularly shy person, reserved, yes, but not shy and timid. I'm just like this in my romantic life. lol. In all other aspects, career etc, I get what I want. If I decide to come out with it bluntly, I can just see myself psyching myself up for a phone call and then bottling it and ruining it even more. I would love to give him a hint and see if he picks it up.

 

Thanks for your responses.

Edited January 5, 2015 by rara

[DivorcedDad123]

I'll vote against telling him by phone.

Find out when he's coming home and plan a dinner at your place. Make him a meal that he loves as a way of welcoming him back. Make sure you're still cooking when he arrives and use the time in the kitchen together to make physical contact. See how he reacts and let nature take its course. If he's interested,he'll make time.

[Frank2thepoint]

I'm pretty reserved and am not sure I could have the courage to say it explicitly. What's the best way?

 

You can write an email, but it's impersonal. So is text. You don't need to have some perfect setting, just ask him out for coffee/tea and/or pizza and tell him that you have feelings for him and want to see if he is interested in being romantic.

[rara]

Thank you guys. I really like DivorcedDad123 answer but I'm afraid we really won't be able to meet. That would be ideal for me, get together, see what happens and then maybe bring it up in person and gauge his reaction. I know it sounds crazy but but, without going into details, work is so nuts for him that he is barely home and there's absolutely no way around that. I just know that we won't be able to meet up until mid March at the earliest. Unless I take a trip all the way to see him which I think just looks weird...

 

So, do I wait and risk him carrying on with life thinking there's nothing between us for 10 plus weeks, or I do I blurt it out over the phone? At this moment I'm thinking I have to say something over the phone. I'm just not sure if this should be a major hint, or clearly 'I think we should think about giving it a go'.