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Should I ask him out?

I started talking to this guy roughly three years ago... he kept asking me out but it took me a few months to agree to a date so he was really patient with me. In that time we still spoke every day. The actual date went pretty well but something happened towards the end which screwed it up a bit and so we didn't really talk after... I was really gutted as I did like him a lot.

I still think about him from time to time and decided to follow him on instagram the other day. He followed me back straight away. We then exchanged a few messages (I initiated the conversation) but then it ended quite quickly as he didn't really make an effort to continue the conversation. Since then though I've noticed he is usually the first to view my instagram stories and he likes all my photos.

As far as I'm aware he's been travelling a lot the last few years so probably hasn't been in a position to settle down, and I can see from his friend's comments that he is still single. I just can't tell if he is still potentially interested. When we met up before it was in my uni town (where he was working temporarily) but we've both now moved back to our hometowns which are very close. I don't want to look too eager, but at the same time I'd like to give it another shot. I'm not sure if it's worth messaging him and asking where he is these days, and taking it from there i.e. asking him if he'd like to meet up one day? Or would this be a bit strange 3 years on?
Original post by cupofcoffee
I started talking to this guy roughly three years ago... he kept asking me out but it took me a few months to agree to a date so he was really patient with me. In that time we still spoke every day. The actual date went pretty well but something happened towards the end which screwed it up a bit and so we didn't really talk after... I was really gutted as I did like him a lot.

I still think about him from time to time and decided to follow him on instagram the other day. He followed me back straight away. We then exchanged a few messages (I initiated the conversation) but then it ended quite quickly as he didn't really make an effort to continue the conversation. Since then though I've noticed he is usually the first to view my instagram stories and he likes all my photos.

As far as I'm aware he's been travelling a lot the last few years so probably hasn't been in a position to settle down, and I can see from his friend's comments that he is still single. I just can't tell if he is still potentially interested. When we met up before it was in my uni town (where he was working temporarily) but we've both now moved back to our hometowns which are very close. I don't want to look too eager, but at the same time I'd like to give it another shot. I'm not sure if it's worth messaging him and asking where he is these days, and taking it from there i.e. asking him if he'd like to meet up one day? Or would this be a bit strange 3 years on?


Just tell him that you want him to be the father of your children and to be known as Mrs -------.
I suppose there's no harm asking to meet up but maybe don't expect much to come out of it if he lets the conversation run dry. You'll never know until you try though.
Original post by cupofcoffee
I started talking to this guy roughly three years ago... he kept asking me out but it took me a few months to agree to a date so he was really patient with me. In that time we still spoke every day. The actual date went pretty well but something happened towards the end which screwed it up a bit and so we didn't really talk after... I was really gutted as I did like him a lot.

I still think about him from time to time and decided to follow him on instagram the other day. He followed me back straight away. We then exchanged a few messages (I initiated the conversation) but then it ended quite quickly as he didn't really make an effort to continue the conversation. Since then though I've noticed he is usually the first to view my instagram stories and he likes all my photos.

As far as I'm aware he's been travelling a lot the last few years so probably hasn't been in a position to settle down, and I can see from his friend's comments that he is still single. I just can't tell if he is still potentially interested. When we met up before it was in my uni town (where he was working temporarily) but we've both now moved back to our hometowns which are very close. I don't want to look too eager, but at the same time I'd like to give it another shot. I'm not sure if it's worth messaging him and asking where he is these days, and taking it from there i.e. asking him if he'd like to meet up one day? Or would this be a bit strange 3 years on?



Personally I think you are in a no lose situation. You reached out and followed him and he followed you back (check 1). He watches your Instagram stories and likes your photos (check 2). He did at least initially respond to your messages (check 3). So, if you decide to ask him to meet you for coffee or something equally casual and he turns you down it's been three years you don't have the same strong feelings you may have once had so you probably won't be gutted. If he turns you down so what, really. But, he might say say and you have a nice time.
I'd just say ______ we haven't chatted in a long time and I see you back in (his hometown) was wondering if you'd like to me up for a coffee. Be light and cheerful.... no drama..... whether he says no or yes. Cheerful and positive. Good Luck.

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