How do I get him to hang out? Should I throw in the towel?

[Anonymous]

There’s this guy I’ve know since high school, he’s extremely attractive! We talked on & off, never actually hung out then. We’d try but nothing ever stuck. A few years ago we reconnected through mutual acquaintances. We hung out he was chubby then then he expressed he wasn’t feeling very confident about seeing me while he felt a certain way about himself. We ended up chatting & he added me on instagram but we mostly chat on fb. We talk everyday & he knows I’m pretty anxious about hanging out again. But he flaked & apologized that he’s been going through a lot. A mutual friend said he doesn’t want to really be seen since he’s much bigger now but I don’t care he’s still attractive to me! I kinda voiced that there’s nothin that can make me not want to see you. He said he knows he just needs a little time. Should I just wait or let it completely go?

[Anonymous]

Assuming your age is correct and you’re also in your 30s, that means it’s been over 10 years since high school. 10. Why at no point in time has dating, or anything else happened?


I understand having insecurities, but as a grown, 30-something year old man, unless he gets professional help (and if he’s being honest of course) then all those feelings are apart of who he is. He’s spent his whole life becoming that person. To which I’d say, when can you expect his personality traits that allegedly keep you apart to change? And why would you want to wait for that to happen?


At this point, I believe he doesn’t have the intent to further your relationship because he would’ve done it already, not repeatedly flake and string you along. Then you are so outward with how bad you wanna see him and how much you like you, you suck the value out of your presence in his life because you are chasing him noticeably. What is there about you for him to miss or worry about losing if it is available to him no matter how disappointing or disrespectful how he is? Looks can only get him so far, accountability needs to start entering the equation.

[Opinion Owner]

****how much you like him

[Asker]

Well after many years we’ve dated other people, he’s moved out of state & became a very successful man. I guess I’ve been curious about him because he’s never mean about anything or has always been apologetic. I take into consideration that his life has changed as well. He was athletic & a sports fanatic which I am too. So it’s not just his looks. I meant that no matter how much his appearance has changed that it doesn’t matter to me. I did catch a glimpse of him so I don’t think he’s lying about anything. How he makes sure he keeps in touch makes me hope he’s curious about me too.

[Opinion Owner]

So no where in the midst of dating other people he actually worked towards dating you? I don't know, I feel like a lot of this reasoning is just excuses in disguise, because he is so nice and seemingly sincere so you wanna give benefit the doubt. When he may not even deserve it.

Listen, it’s very possible to be a good guy, but as a boyfriend, he really sucks. Both versions of him can exist and I think you get the two confused. You excuse a lot of his behavior because it’s delivered to you in such a kind, apologetic nature. But at some point you have to take a step back out of your romantic, empathetic feelings, look out for yourself and say ‘hey, it’s kinda messed up that he keeps making excuses to bail on me or not make a solid plan. Kinda messed up for him to hear how much I’d like to see him and don’t care about his looks her keep falling through.” You deserve to have a certain standard set as well, and to be shown that you aren’t wasting your time.

[Opinion Owner]

***you’d like to see him

[Oliverlogan263]

Hmm, that's a tough one babe. On one hand, I understand his insecurity about seeing you again since he's gained weight. That can really mess with a guy's head, even if inside he knows you don't care about that stuff.

But at the same time, all this flakiness would be frustrating for sure. You've made it clear you're still into him regardless, so props for that. I think maybe give it a bit more time, but also start keeping your options open just in case.

How about you ask him to a low-key thing like getting coffee? Low pressure way to break the ice without a big "date" vibe. Or suggest doing something active together to boost his confidence, like going for a hike or cooking a healthy meal.

If he keeps flaking even little meetups, you might have to call it. Don't wait around forever, you know? But seems like he really likes you deep down. Hope he gets his stuff together soon! Keep me posted on what happens, girl.

[Asker]

Thank you so much! This is very helpful!!!

[Oliverlogan263]

No problem girl! We've all been there chasing after a hot guy who's kinda flakey, so I totally feel your pain. Dating can be so frustrating sometimes. But you seem so sweet and you deserve someone who wants to spend time with you for sure.

I hope putting a deadline on him works to either get him to step up or let you move on. But either way, don't lose that confidence - you're a total catch and there will always be other guys who see that. Sometimes these dumb high school crushes just don't work out, no matter how much we pine after them!

Chin up, stay busy with your friends and posting fire selfies. And please keep me posted on what happens - I'm invested in your love life now! You've got this sis. Message me anytime if you need an ear or some encouragement. Xoxo

[Asker]

Hey so I have an update! We still be chatting but haven’t hung out. I did end up getting a little fed up waiting so I just put it out there that I don’t care what he looks like I have always liked him. He said it really meant a lot to him & he has a close friend who just found out about cancer so he’s been in his head a lot & said he didn’t want me to find someone else while he’s been trying to work out his mental issues. At first I was thinkin maybe it would be something that just would be physical anyway but we have been getting to know each other very well along the way & I feel more ok with giving him the time he needs. I still keep other options at bay though lol but I’m glad I stuck it out to hear him out even though I had to push him a bit a few times

[Anonymous]

I say move on.