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You Asked: Love Lost and Found

Dear Sugar,

An old friend has come back into my life. We were a serious item in high school and part of college, but instead of being a gentleman and breaking up with me maturely and civilly, he turned into a self-centered jerk and broke my heart.

A decade later, we're talking again. We both have grown up a lot, settled into our careers, and had our fair share of broken hearts, and we are both still single. We have started a friends with benefits relationship, but the problem is I feel like I'm falling in love with him. When I meet other people, I constantly compare them to him. Our friends tell me that he may be wanting more; however, I'm not sure if I want to be with him on that level purely out of self-protection. I know everyone deserves second chances, but I just don't know what I should do. — Blast From the Past Blair

To see DearSugar's answer

Dear Blast From the Past Blair,

Your relationship with this man sounds very complicated, so the best advice I can offer you is to talk openly and honestly with him about your feelings. We all know that friends with benefits can lead to a lot of confusion and often times a lot of heartache, so make sure you're on the same page before history repeats itself.

Just because you're in each others' lives again, you don't have to make any decisions on your relationship status just yet. Being cautious with your heart is a totally normal reaction, but if you think you're falling in love with him, you owe it to yourself to explore this relationship — like you said, we all deserve second chances. If at the end of the day it doesn't work out, at least you'll know you tried. Good luck to you.

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RockAndRepublic RockAndRepublic 8 years
I don't get how he gets compared to other guys when he treated you like crap. What exactly are you measuring.
cloeyxd cloeyxd 8 years
Okay... My advice is really simple: Find out whether he would consider making your relationship more seriously. You don't even have to tell him how you feel, just drop it into conversation as idle ponder, as it were. If he says that he would consider doing so then perhaps set up a few dates and see how things go. If he says no. Break things off. Immediately. I know it's hard, but you can't let him break your heart again. If it's still possible for you to stay friends then do so, but it'll probably be hard not to slip into the same old pattern. Good luck. I hope it all turns out well for you.
cloeyxd cloeyxd 8 years
Okay... My advice is really simple:Find out whether he would consider making your relationship more seriously. You don't even have to tell him how you feel, just drop it into conversation as idle ponder, as it were.If he says that he would consider doing so then perhaps set up a few dates and see how things go.If he says no. Break things off. Immediately. I know it's hard, but you can't let him break your heart again. If it's still possible for you to stay friends then do so, but it'll probably be hard not to slip into the same old pattern.Good luck. I hope it all turns out well for you.
CoMMember13630786602261 CoMMember13630786602261 8 years
that was supposed to say you *might* find the same..
CoMMember13630786602261 CoMMember13630786602261 8 years
I dont really have any advice, just support. My boyfriend and I have known each other for 5 years. We dated for over 2 years, broke up for almost 2 years and now have been back together for almost 1 year. We kinda remained friends during the time we were broken up (basically just calling eachother every few months to check up) We both had other relationships during that time (very bad relationships) We both got out of our relationships at about the same time and started talking on a regular basis again. We talked about getting back together, but there were still some issues that were keeping that from happening. Finally we both realized that we were just wasting time not being together, and have been back together ever since. Its funny though, because when we first broke up, I thought he broke my heart...he thought I was the one doing the heartbreaking...you mind find the same if you talk to him about it.My best advice would be to just keep open and honest communication with him. Let him know how you are feeling..(but dont over do it) Other than that the only thing you can do is wait and see what happens, it will work itself out one way or another. I just wanted you to know that it is possible for love to come around twice... and its even better the second time around!
almost-famous almost-famous 8 years
LOL girl and it fits this issue so well! :)
sofi sofi 8 years
that's very funny, because I just used that saying for someone else I know-lol!
almost-famous almost-famous 8 years
Yeah i know its been awhile since they've known each other, but as a woman She should wait because women usually develop feelings during intimacy. Its not like they're teens. He's a MAN he's not stupid. If he knows how to go about scoring correctly during his old final exam tests in college, then he knows how to tell a woman he got feelings. Whether its inviting her over for lunch (with no sex included) or a weekend getaway. Age has nothing to do with it, I believe if you have feelings for someone you're going to be with them...But he seems to be getting the milk for free...(you have to know the old saying inorder to get it) LOL ♥LOTS OF LOVE♥
almost-famous almost-famous 8 years
Yeah i know its been awhile since they've known each other, but as a woman She should wait because women usually develop feelings during intimacy. Its not like they're teens. He's a MAN he's not stupid. If he knows how to go about scoring correctly during his old final exam tests in college, then he knows how to tell a woman he got feelings. Whether its inviting her over for lunch (with no sex included) or a weekend getaway. Age has nothing to do with it, I believe if you have feelings for someone you're going to be with them...But he seems to be getting the milk for free...(you have to know the old saying inorder to get it) LOL ♥LOTS OF LOVE♥
Belle1031 Belle1031 8 years
Everyone deserves a second chance. However, don't let there be a third. Good luck. :P
sofi sofi 8 years
almost famous- I don't know about waiting. These people have actually known each other for a really long time so there is more here than just FWB. there has already been heartache obviously, so why let it go on any longer. It sounds like (from my calculations) they are both in their early thirties- will this go on for another decade. It would be different if they had just met and having a fun relationship, but don't let this go on for another decade- my opinion :)
sofi sofi 8 years
ok, you are both hopefully a lot more mature than you were in high school and college so you need to talk about this. You've obviously always thought about him and need to sort through your feelings. He hurt you bad and you probably couldn't deal with that again, so for your own 'self-protection' (as you put it) be completely upfront with him. Sit him down and tell him how you feel now but how he hurt you in the past- which you never complete got over. Guys take a while to mature and he may be a completely different person than he was in his teens. You need to get a clear indication from him that he realizes what he did was wrong and hurt you and he wouldn't do that again. Considering your history, you can't go on with the friends/benefits thing very long. Get it out there and if he doesn't want more, I would get out otherwise you will continue being heart-broken and thinking about this one guy. Good luck- this is tough but figure out what you want from him and talk about it.
sofi sofi 8 years
ok, you are both hopefully a lot more mature than you were in high school and college so you need to talk about this. You've obviously always thought about him and need to sort through your feelings. He hurt you bad and you probably couldn't deal with that again, so for your own 'self-protection' (as you put it) be completely upfront with him.Sit him down and tell him how you feel now but how he hurt you in the past- which you never complete got over. Guys take a while to mature and he may be a completely different person than he was in his teens. You need to get a clear indication from him that he realizes what he did was wrong and hurt you and he wouldn't do that again. Considering your history, you can't go on with the friends/benefits thing very long. Get it out there and if he doesn't want more, I would get out otherwise you will continue being heart-broken and thinking about this one guy.Good luck- this is tough but figure out what you want from him and talk about it.
almost-famous almost-famous 8 years
While Dearsugar usually give GREAT advices, I don't know about telling him your feelings YET! I believe you should wait a little while longer and act when HE acts on his feelings. Let him invite you over to his place and just chat. Usually F.W.B's never just invite you over for a long conversation and NOT have sex. Right? Well if I were you I'd wait till he said something first eventhough hes a bit more mature. STILL WAIT!
almost-famous almost-famous 8 years
While Dearsugar usually give GREAT advices, I don't know about telling him your feelings YET! I believe you should wait a little while longer and act when HE acts on his feelings. Let him invite you over to his place and just chat. Usually F.W.B's never just invite you over for a long conversation and NOT have sex. Right?Well if I were you I'd wait till he said something first eventhough hes a bit more mature. STILL WAIT!
Jeny Jeny 8 years
Wow! Good luck with that!
Jeny Jeny 8 years
Wow! Good luck with that!
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