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My confidence issues are stopping me asking for a date.

Tagged as: Crushes, Dating, Troubled relationships<< Previous question   Next question >>
Question - (7 November 2017) 7 Answers - (Newest, 20 November 2017)
A male United Kingdom age 30-35, anonymous writes:

Started messaging a girl I knew from school a few years younger than me around 3 months ago but she'd just gone travelling. It was fun and kept it up throughout her trip and her interactions with me on social media increased so thought she might be interested. I wasn’t really flirtatious or sexual because I'm shy and lack confidence, mainly I just messaged her about what she'd been up to and made general conversation, probably not good in hindsight. At one point she opened up about to me about mental health problems which I suffer from too so I gave her quite a bit of support with that.

When she came back from travelling she went straight back to uni and from then on her interactions with me decreased and she wasn't talking as much and took longer to reply when I messaged her. I asked if she was interested in going for coffee when she was back (meaning as a date although I never said it explicitly) and she agreed and gave me a weekend so a couple of weeks later I messaged her again and set it up.

On the "date" I was nervous and my shyness probably came across, she's shy too and was quiet when I was talking to her. I wanted to come across confidently but I don't think I did, not as much as I wanted to anyway. Still, it was mostly alright except she said she'd being seeing someone "just for the past few weeks" which completely deflated me. I couldn't read any signals either way when we were messaging or on the date, apart from that one. She's still single on facebook so it's not that serious *yet*. I don't think she thought it was a date really although she'd made herself look nice. I messaged her the day after saying I loved seeing her and I'd like to see her again over Christmas if she'd want, she replied just saying it was so lovely to see me.

I'd be tempted to cut it off because she's so far away so often and now she's seeing someone but I do really like her and have done for a long time but she was in a relationship for a long time until summer. I don't really know what to do now, my plan was to ask her again in a few weeks for when she's back at Christmas to do something more intimate that's more date-like but I wouldn't want her to get serious with the other guy in the meantime. I've asked friends for advice, one of them says if she's seeing someone I should tell her now or never but I don't really want to say it directly, especially not face-to-face, and risk losing a friendship? Another said I need to make something happen and ask to go and visit her but I don't want to be that forward and to be fair I really can't read her signals either way (apart from the obvious "seeing someone") which is why I want to pursue her, plus I do really like her. A female friend said she might not have thought it was meant to be a date and I need to build the courage to tell her how I feel but so many articles online say don't do that, and she also said I could ask her to travel over one day or just wait til she's back and give some indication it's a date. My confidence issues are what’s stopping me really, I’ve been suffering with depression for a couple of years and made a breakthrough a few months ago to start moving forward and out of my comfort zone – dating and doing stuff with girls is one of those things, I’d never tried anything in the past due to being so shy so this is my first time in the game really. I would like to tell her but her being so far away so often and risking that rejection and her perceiving it as weird if she was never interested, plus showing that vulnerability and facing rejection and being creepy... I just don't know what's best.

View related questions: a break, christmas, confidence, facebook, flirt, shy

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A male reader, Sam Wilson United States +, writes (20 November 2017):

Sam Wilson agony auntSorry to hear that Bro, but yeah everything we said here still remains. If you think a girl is worth it, just do it. Sometimes all shyness and fear needs to get out of the way is a single push.On the meantime I suggest working on your confidence.

I wish you the best of luck in your future endeavors

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A male reader, anonymous, writes (15 November 2017):

They're now facebook official so yeah, that's that. Could say more but what's the point. Gonna have to move on now whether I like it or not. I've learnt a lot though so I can take something from that, hopefully if she becomes single again I'll be better equipped because these feelings ain't going anytime soon.

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A male reader, anonymous, writes (10 November 2017):

Cheers for the advice everyone.

I'm well aware that confidence is a big thing and I am working on it but it's virtually like trying to become a whole new person when the only life you've known is a shy one. I always knew the distance would be a stumbling block and the reason I didn't move quicker was more lack of experience than lack of confidence, instead thinking "well I won't have a chance to see her so I can't ask," kinda regretting it cos looking back I'm sure there was at least some interest but at the time I couldn't decipher whether she was just being polite. When she stopped being as responsive I thought either she had been interested then met someone else or was never interested and just forgot about me or got involved with uni people but that doesn't hold. And I will stop overthinking one day.

The consensus seems to be tell her, unless she does get more serious in which case I won't. I'll give it a few weeks to focus on more important stuff and because it'd be a bit weird out of the blue when it's gonna be over a month until I could see her. It does kinda feel like the moment's passed but if I don't say anything I think I'll regret it for a long time, it's a risk I have to take.

Thanks again.

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A male reader, Sam Wilson United States +, writes (8 November 2017):

Sam Wilson agony auntSorry bro but Im saying this as sincere and nice as humanly possible...you have missed your shot and Im sure we are all very sorry for you.

With her being far away, seeing someone (event though they arent bf/gf yet), and you starting out approaching her as like a friend; all signs point to a rough battle.

I dont believe those columns saying dont tell her how you feel.As someone who also had mental problems dealt with in the past please dont let it bother you, I know its cliched but be confident...make a CHOICE,make a STAND,OWN your ACTIONS, thats the only thing we could ever do.

Never let the opinions of other people affect your path to happiness if you know youre morally right, be true to what you want . Will it make you feel better to tell her how you feel? Because honestly for me if its eating you up inside I think you should give it a shot. Dont tell her you want to be with her but rather tell her what you feel, what she means to you. If you fear rejection and vulnerability then you have a choice to make. Is she worth the time, effort, vulnerability and pain? Can you risk being crushed for a chance of happiness? Im afraid its a situation everyone has to face eventually and youre not alone.

I really hope you can make that choice, be brave and take that chance with her...if not her then maybe for somebody else special that comes your way in the future. Good Luck.

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A female reader, Dionee' South Africa +, writes (8 November 2017):

Dionee' agony auntTo me, there´s a bit of a problem here. Not to knock your confidence or anything but you´ve been way too slow with this situation.

Ever wonder why ´alpha males´ get the girl? It´s because they ooze confidence. There´s no wondering whether or not it´s a date with guys like that. Which leads me to my point; when asking out a female, let your intentions known... in other words let her know that it´s a date date and not just a hang out which is something I think that you didn´t do this time.

You should always make your intention to date very clear or you will quite simply, be overlooked.

I say, if she seriously is seeing someone then back off for a bit as coming on too strong will be disrespectful and it might knock you down a few points rather than gain points for you.

Perhaps you´ve missed your chance for the time being. I´d say wait this relationship of hers out and try to be her friend. In the meanwhile, try to date other females and go out with friends and you just might meet another lovely girl whom you may grow to fancy.

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A male reader, N91 United Kingdom +, writes (8 November 2017):

N91 agony auntFirst of all, stop reading columns and doing what your friends tell you to do. Since when is there a set routine of what to do and what not to do? I'm gonna be completely honest and say you've friend zoned yourself by being too slow off the mark. I understand you don't feel super confident, but from what I've evxperienced over the years that's a real turn off for females when a guy just pussy foots about. I have been there when I was younger I've been through lots of rejection and learnt from it.

If she's comfortable enough to tell you she's seeing someone else then I'd see that as a major sign as she only sees you as a friend. I think if she was romantically interested in you she would make it known and she DEFINITELY wouldn't be telling you that there's other guys in the scene. If you're worried about losing the friendship then you've already been defeated because that means you're not going to be willing to take the plunge and ask her where you stand. This is what finding love is all about man, taking chances and believe me it rarely goes the way you want it to, but that's what dating is about and weeding out people who aren't right for you.

I learned quickly over the years what kind of behaviours to stop showing to the females and I noticed my fortunes changed heavily. You need to put yourself out there, you need to be more assertive and know what you want, you need to be willing to let them know what you want and if they don't want the same thing as you, you need to know when to cut things off, dust yourself down and move onto someone else that wants the same things as you.

If this is the first girl you've liked then believe me I understand, I've been there, everyone has. Personally, I think this one has run its course and she's only ever going to see you as a friend. If I were in your shoes I'd just be upfront with her and tell her how you feel and you want to take her on an actual date. That was she has to be honest in return and you finally get your answer of where you stand.

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A female reader, Youcannotbeserious United Kingdom + , writes (8 November 2017):

Youcannotbeserious agony auntOh sweetheart. Sending you a huge hug. If other-thinking was an Olympic sport, you would be right up there on the rostrum. Your desire to get it absolutely "right" is paralyzing you.

The only person who never made a mistake or never got it wrong is the person who never actually did anything. We all make mistakes and all experience rejection in life. Part of growing as people is experiencing these things and learning how to deal with them.

Obviously we don't know the young lady in question and how she perceives you. She obviously doesn't dislike you otherwise she would not have stayed in contact with you for so long. She may see you as a good friend. She may see you as a potential boyfriend but be too shy to make this obvious.

Personally I would not lay too much importance on her statement that she was dating someone. This could be a five minute wonder. It could also have just been her panicking and saying it so that YOU didn't think SHE was trying to pursue YOU. You could both be pussy-footing around each other due to your shyness.

In your shoes I would stay in contact, stay friendly, and try to spend some time together when she is back home.

In the meantime, however, I would try to get out and about more with friends. You have heard the saying "don't put all your eggs in one basket" I am sure. You never know where you might bump into someone who takes your fancy. Go out with the aim of enjoying yourself and have a good time. Then whether things move forward with this young lady or not will not be quite as important to you. Most importantly, remember we ALL suffer rejection or get things wrong in life. It is part of life. Don't be so afraid of making mistakes that you do NOTHING. Regrets about missed opportunities are far stronger than about trying and getting it wrong.

Good luck.

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