To date a friend?

[Earlgrey19]

I’ve recently reconnected with a lovely male friend who is also single, we spent a long evening together in which we both felt very close. He sent me a message afterwards saying ‘it was so lovely to reconnect, more soon please.’ I’d love to spend more time with him and just see where it goes. I wasn’t quite sure if he was just messaging me as a friend, though. I’m afraid of being inappropriate or too much if I suggest meeting up too soon. I was hoping he’d suggest something and he hasn’t. I also want to make sure I’m not rebounding since he’s a friend I care about.

I’ve been through a hell of a lot of stuff in my personal life over the past few years, including marital separation, then someone else pursuing me and breaking my heart, and my friend knows that and I sense he is being careful with me.

I saw him 2 weeks ago and wanted to see him this weekend but was afraid he’d find it too much.

I got the sense he is interested in me beyond friendship but am afraid of misreading or doing the wrong thing. From being his friend I know he can overthink relationships. I’m aware he could be having doubts. Then again he tends to do a lot of online dating and I kind of don’t want to miss the boat… !

What would you do?

Sounds like he's interested in getting closer. Make it clear you're interested before its too late. Maybe ask his plans for the weekend, tell him you fancy a date night and wondered if he's free.

Friendship is THE BEST starting point for a successful long term relationship. My husband was my best friend first. It’s easy, relaxed, secure and wonderful.
Go for it.

Thanks! I think I want to. But also know I’m lonely. If he weren’t a friend I might let myself just explore and see where it goes. Bit afraid of hurting him, and a bit afraid about getting hurt myself. But seems a shame not to try…

Why are you so scared of appearing to want more, when you so obviously want more? Get rid of that insecurity which is burdening you and go for it, girl!

Thanks. I had replied to his ‘more soon message’, with ‘yes let’s definitely hang out sometime’, but I also made it quite a jokey, friend like message & he hasn’t replied. So I’m not sure whether to follow up more or if really he’s not interested. I know I sound about 15 years old about this!

Wait for him to respond now. Hope it works out for you

Just drop him a message. Is there something on locally that you can make a tentative link about and message him?

Thanks @MyOtherProfile I think I’ll try that. He lives in London & I don’t but I’m there quite a lot & can come up with something, or just suggest a walk, maybe…

You don't have to make it obvious over the phone, just a light "got some time to reconnect again this weekend?". Probably easier to gauge the situation in person. How you both feel will become evident the more time you spend together, and anyway, might be better and more fun to not rush to it, so take your time.

I dated my friend, he’s my DH of 25 years this October. I nearly knocked him back for a date as I didn’t want to ruin our friendship. I’m glad I didn’t. Go for it OP

I also dated my friend. We've been married over 30 years now

Another one here who agonised about dating their friend but still together 17 years later. I think friendship can be a wonderful foundation to build a loving relationship on.

Update on this:
I have spent a bit more time with him, and it kind of feels like there’s sexual tension, but so far we’re still just friends. He invited me to an extremely fancy night out that he’d got free tickets for, very romantic setting, and included champagne picnic, and then he suggested I come along on the weekend he was going to visit a mutual friend of ours by the sea, which I did, but nothing has happened. And it turns out that during this time he’s been on 3 dates with someone whom friends introduced to him as a blind date, but feels he’s not sure he has chemistry with her and doesn’t know what to do. He told me about this on the train home. He asked me if I was dating or not ready. I told him I tried OLD but not sure it’s for me.

So, I’m slightly confused as I felt he might be interested at first but in the end perhaps he only thinks of me as a friend?
I have given really no signals, apart from coming along on these two things he suggested, as I’m terrified of making him feel uncomfortable, or being rejected. Still slightly unsure whether I should get over myself and risk being more bold sometime, or just leave it as probable that he’s only interested in being friends.

I do have a shitload of background stuff: slightly crazy ex, Dad to my 2 kids, who may not survive as he had advanced cancer and is at risk of recurrence, and can be very difficult, which my friend knows, so I also wonder if that is offputting to him (and any possible future partner).

You need to relax. Spend time with him. If he's the right person for you, you won't be spending forever in torturous indecision. Something will just happen. You're in danger of worrying so much that you'll even hide the fact that you like his company as a friend!

If you're this anxious about it all, maybe it's not the right time for you to be getting into something? And if you are, it'll be with someone who puts you at your ease, not someone who has you feeling like you're not surefooted.

Lots of your posts are wondering how he feels. How does he make you feel? Wanted?

Great reply, Foundations, thanks.
I feel I want him. I feel attracted to him, though very used to him just bring a friend. Feels like we’re developing more emotional closeness, learning more about each other. Does he make me feel wanted? He’s been amazingly supportive through my family troubles and I’ve felt very cared for and cared about. I think that part of my anxiety is that 17 years ago as students we were in an ambiguous friendship but in the end he decided we were better just as friends. He told me way back then that he thinks I’m gorgeous but that we’re maybe quite different. That was 17 years ago, though and I don’t think either of us quite feels quite the same person we were then.

Another part of my anxiety is that he’s also so proactive about online dating etc that I feel I might lose the chance soon!

Why not just ask him, 'Why don't you think anything has ever happened between us?'

That's non committal yourself but could be construed as flirty, or at least 'thoughtful' if he responds well....

It sounds like he's interested to me from the above!

I massively agonised over dating my friend who was the nicest man I knew, because I didn't want to ruin the friendship / make things weird and awkward. We've been married three years (and he's still the nicest man I know) :)

He might deliberately be continuing with OLD as a way of not pressurising you into something more, little knowing it has the opposite effect.
I'd have a heartfelt conversation and go for it, just let him know how nervous you are and progress at a speed you're comfortable with. Good luck!xx

But your anxiety is a fear of doing/having something done to you that will make you feel bad, right?

Only do things with him that feel good. Go to places you feel good, at the time of day that feels good, in clothes that make you feel good, for the amount of time that makes you feel good. Don't tie yourself up in what might make him feel bad. If he's good for you, he will be happy doing things that make you happy. Communication will be open, so you'll know when he's feeling happy too. Then you'll be able to clearly see if you match up or not.

Currently, with such concerns, you're likely to do things that make him happy and pretend to be happy yourself when you're not. That's an anxiety recipe.

An anxiety-squashing recipe is focusing on your own feelings, spending more time where you feel good, and withdrawing when you feel bad. Your feelings are very good signposts; after all, all the things you want are feelings. Happy/content/excited/fulfilled etc. Feelings are really all we have.

If you've been out with him a coupe of times, and he gets together with someone else via OLD, he's not into you enough. It's a mismatch, because you're spending your evening worrying about him, whilst he's spending his evening with someone else. It wouldn't be 'losing him'; it would be having him filtered out of the running, because he's not right for you.

Yes, good point, Foundations, and that could be the case.

He’s going abroad now for a month, so I won’t see him for a while.