He is lovely but very shy. Should I ask him out?

posted 3 months ago in Relationships
Post # 31
Member
1750 posts
Buzzing bee

So I discussed this with my husband, as he typically can be really thoughtful in his interactions with others and has good insight. In his opinion, he had a hard time asking friends out because he genuinely enjoyed the friendship and he didn’t ever want to come across as a creep or make women feel uncomfortable around him. Whenever a woman was interested in him, they usually had to really spell it out or he would err on the side of assuming everything was friendly. He said that getting an invite to go to a certain event would not leave him thinking the woman was romantically interested, but only that she was expanding the friendship to hanging out at events together. Complicating things further is that he is part of a volunteer group that is really close, and it’s possible that he needs to be really sure before making any moves because if he is reading your signals wrong, you might be uncomfortable around him and there might be tension within the group in general. 

So yeah. Actually ask him on a date and see what he says. 

Post # 32
Member
2110 posts
Buzzing bee

I would send him a message and say something like “I felt like when I saw you today it was a little bit awkward. I’m sorry if you felt uncomfortable after I asked you on a date and I completely understand you just want to be friends”. This way, if he is interested he will say so otherwise you have your answer. 

 

Post # 33
Member
993 posts
Busy bee
  • Wedding: September 2020

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strawberrysakura :  I agree with this. It’s really putting yourself out there, but I would say something that implies it’s the time you would spend together that you would enjoy (more than the event). Like, “it’d really be nice to get together for coffee sometime when we have a little more time to chat.” 

Post # 34
Member
566 posts
Busy bee

I’ve never been one for playing it cool or hard to get. If I liked a guy and thought he was interested too I would make it very clear. I’m also socially awkward and shy, so 99% of the time it would by by text message (maybe your guy would feel less anxious communicating by text). But I’m a big believer that if you have feelings for someone not to hold back, there’s nothing worse than looking back and wondering “what if?”. Asking scary questions by text message is so much easier than face to face. If it was me I would just put it all out there and make it really clear, that you like him and would like to go on a date and ask if he is interested. Some guys really are shy and awkward and need you to take the lead in the beginning at least. I personally would rather get a clear no then move on, than be unsure and waste energy and time wondering. Really hope it’s a good news for you though ❤️ Good luck!

Post # 36
Member
993 posts
Busy bee
  • Wedding: September 2020

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magiccircle :  That seems like a great sign – how exciting!

Post # 37
Member
1750 posts
Buzzing bee

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magiccircle :  That’s obviously a great sign. But for goodness sake, ask him out on a DATE. Otherwise he will assume YOU are thinking this is just a friends thing. 

Post # 39
Member
1750 posts
Buzzing bee

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magiccircle :  Just send him a message online and say, “Hey event x is in 3 weeks. Would you like to get together sometime before then?” That’s it. That reads more as date than ‘I’m inviting you to this event possibly as friends because you might like it’. 

I would be shocked if he said no. If he really isn’t interested he will say, sure, and then not really make any suggestions or if you suggest something he will find a way to be busy and will be brief in his conversations with you. That’s your cue to act like nothing happened and it will blow over. 

But I REALLY think he wants to go out with you, so I think he would say yes and either suggest a time, or if you suggest a time he will agree to it. That will bring you closer to dating.

I get that this is tough, I had to make most of the first moves with my husband, but once he was SURE that I was interested in more than just friendship he was very clear about how he felt and didn’t hold back. 

Post # 41
Member
1750 posts
Buzzing bee

Do it today! You’ve got this! No point in waiting and wondering. 

Post # 42
Member
11349 posts
Sugar Beekeeper
  • Wedding: City, State

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magiccircle :  

I would just stop for now.  If he’s as shy as you say, he’s going to feel uncomfortable with anymore approaches for now.  Let things gel.

If the event is on a weekend, 10 days notice is ok.  Don’t send him cute little reminders.  Not until you are Official.  Then you can send anything.

And dear gawd, no emojis.

If it’s a weeknight thing, seven days is ok, unless there is heavy planning involved and/or traveling.

I disagree with Team Go For It.  They’re not factoring in how shy the guy is, which means he can be easily overwhelmed.  Overwhelm = falling back.

You do not need anymore answers today.  You can let things evolve organically.

He opened the door, you made an agreement to attend an event together.  Let it happen.

Post # 44
Member
1750 posts
Buzzing bee

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sassy411 :  I don’t know, I know a fair amount of shy people and what they are usually looking for is an opening that they can’t rationalize their way out of. The shy men I know just want to know that the girl is truly interested, and it’s more overwhelming for them to sit around forever wondering if they said or did the right thing, or should they do this or that, or how did the OP feel about things, etc. Every single shy person I know (and I know a few that are so shy that they can literally not say a word to you for weeks because shyness) are nothing but grateful when they don’t have to stress about wondering anymore. I know literally no one who thinks, “I’m so glad they didn’t tell me they were interested in actually dating me because that’s overwhelming.”

However, I don’t know every shy person in the world and maybe someone does feel that way. 

I think a lot of issues can be avoided if people just communicate, and I see no point in waiting around for weeks obssessing over a guy when you can find out RIGHT NOW if he likes you or not. Sure, it’s scary – potentially being rejected will always be scary. But if he’s not interested then she’s spending a lot of time and mental energy on this that can be devoted to another person or herself, and if he IS interested as I think he is, then they could be going to this event in 3 weeks as an established couple. I think that’s worth a text asking to hang out. 

Post # 45
Member
871 posts
Busy bee

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magiccircle :  

I also am not in favour of you asking this guy on a date unless you want be the one in the driver’s seat of the relationship on a regular basis. Maybe you don’t mind asking for the majority of the dates or making the majority of plans, but that wouldn’t do for me.

You have plans to go to the same event, which is lovely. Personally, I would exercise a little patience until then. You can send a short reminder a few days beforehand which doesn’t require a response: “Don’t forget about _________ on Saturday!”

If he says he can no longer make it, don’t take it personally. But I wouldn’t extend any more invitations to him in a big hurry. 

If he does come, great. I’d take it as an opportunity to have a more subtle approach – talk to him, flirt with him, touch his arm, make eye contact, give him a compliment. Wait for him to come forward a little. I’m a big fan of letting things build slowly and naturally, rather than girls asking guys on dates (and to be clear, if girls want to do that, that’s entirely up to them. I’m just saying am not a fan of it, for the most part.)

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