Welcome to DearSugar's new feature: Handle This. I'm going to give you a hypothetical scenario and ask you to tell me how you would handle it in the comments below. Let's give it a whirl.
You and your boyfriend planned a romantic getaway for your one-year anniversary. The tickets are booked, the hotel is booked, even the tours around the island are booked. Unfortunately, a week before your trip, you find out that your boyfriend cheated on you back when you first started dating. Of course, you're devastated and you break up with him. He's devastated, too, and is relentlessly begging you to take him back. He claims this was just a misunderstanding since it happened before you two were an official couple.

You're torn — you don't know if you should forgive him since it was so long ago or if you should stand your ground since he technically lied to you for almost a year. To add more confusion to the mix, your entire trip is already paid for and you're supposed to leave in less than a week. This romantic getaway could be the perfect way/place to work everything out, or it could turn into a huge mistake and a total nightmare. You don't want the trip to go to waste, but you just don't know what to do. I know this is a toughie, but ladies tell me, how you would handle this?









Radley
Alexander McQueen
Miriam Ocariz
hmmm, well this does sound tricky. however, if what he's saying is true, that he hooked up with someone else before the DTR (defining the relationship talk) then i don't think he cheated. however, if i was his girlfriend i would be pretty bummed that i found out, but nothing is set in stone until you state aloud you are boyfriend and girlfriend, and that you both should not see other people. even if i, the girlfriend, didn't kiss anyone else or even think about it the entire time we were dating, that doesn't mean he did the same thing. i also don't think it's realistic to have expected him to not date anyone else before the relationship was official.
i would still go on the vacation with him, apologize for overreacting, and hopefully start fresh with a new outlook that we both want in this relationship.
BUT, if it turns out that he cheated after we, in fact, had the DTR, i would tell him i needed to clear my head, and head out on the vacay with my bff. what better way to gain some clarity than to put physical distance between myself and the situation, while also enjoying the sun and knockin back a couple mai tais??
1Break up. I would not be able to go on a vacation with him just for the sake of the fact that the vacation was already paid for. Cheating is one thing but he kept it hidden for the longest time; there would've been a chance for forgiveness if he had confessed around the time it happened. // I'd ask him to hand over the tickets and take a girl friend with me.
2Wait, it was before we were a "couple"? Ehh...I'd still be upset but it's forgivable. We're going on that vacation.
3I would go on the vacation still. I might not be the happiest person in the world, and he better be my loyal servent the entire trip, but I could forgive him.
4I mean it was BEFORE being a couple, and boys are boys and rarely think with their heads (well their "real" head, the one with the brain).
hm I would forgive him, I would be upset and he would better make me feel better on that trip!! But yeah I would forgive because he cheated before being a couple.
My boyfriend cheated on me in the beginning of our relationship. I found out 2 years later and I was devastated. It was horrible and I felt bad and I was hurt because I gave him a chance to confess but he never did so he lied to me for two years. I didn't break up with him because of two reason. We have been together for two years when I found out and I had no reason to not to trust him before. Second reason was, he cheated in the beginning of our relationship and I understand he was confused and everything with his ex. I was upset that he got with me if he still had feelings for his ex. But it happened. He kept it hidden from me because he was afraid that I would break up with him. Everyone makes mistakes. I believe in second chances and I gave him one. We are together now for over four years and we both couldn't be happier.
5I think the real question is who paid for the vacation?? If he paid for it - I would go. If I paid for it - I would go and bring a friend instead of him. If we both paid for it, I would go and try to work things out. If it doesn't work then break up.
6break up and take your sister. Than send said jerky boy sweet pics of you in bikini, dancing on bar with hot island men.
7Seriously, hooking up with someone before you were actually a couple? If they hadn't had the RDT (Relationship Defining Talk), anything's fair game. I used to be dating 10 guys at the same time. Even when I first started dating my husband I was dating a lot of men. And we've been happy for 7 years. Why should she even be mad??
8someone explain to me how it was cheating if they weren't even officially together/ exclusively a couple? i don't understand the reasoning for "break up".
9Forgive. Cheating happens. Its horrible and it shouldn't, but if you're not married and if the person in truly sorry, I think its worth another shot. Everyone makes mistakes.
10it's all about the DTR... totally agree with siucra
11i dont get this one...cheating before being a couple?
whatever...I think I would still go, although the idea of someone I trusted for a year keeping these kind of secrets from me is a red flag....
but I would go just to get a f*cken awesome tan.
12It sounds like we weren't officially a couple, so while I would be bummed, I'd let it go and go on the vacation. Maybe a trip together is what I need to get some reassurance of our relationship.
13Talk it out. If it really bothers you to go with him, take your best friend instead!
14You can't cheat before you're a couple..
I'd make him feel REALLY bad for a long time and then get over it. I'd go on the holiday but probably not trust him for a while.
15I completely agree that it doesn't even qualify as cheating if there was no couple. I'd absolutely still go on the trip. I wouldn't even have been "devestated" and broken up with him in the first place.
16Work it out! It was forever ago, and as long as he's been devoted for the last year, it's not a big deal.
17If you weren't technically together, how is it "cheating"? I'd be mildly upset, but as long as he wasn't emotionally attached to someone else, and he USED PROTECTION so as not put me in danger, then I guess there's not too much to get upset about. I'd be pretty grossed out by the thought of someone I loved having had sex with someone else while he was sleeping with me, of course, but it doesn't seem technically like cheating.
18Hmm....I really dont know what i would do- I guess I need to know the exact details (who paid for the trip, blah blah). I probably wouldn't go. I am one of those stick to my guns type.
19So what if it's paid for already? you can go on your own and/or bring someone else.
20why is he telling you now???
this must mean someone feels guilty. which means there are some discrepencies about whether or not you were official.
and i would need more detail on this: was he telling you that you were the only gal during this time?
you know what, i would be mad at him, but i would go on the trip- and give up zero nookie.
the reason why i would be pissed is because you are celebrating to at some extent maybe a lie.
in real life you know the guy would've told you some bullsh*t lie, and made you think he was only into you, and you and him doing couple things and what not. and th truth is, 9 times out of 10, we girls believe that crap because in the beginning, we are smitten.
make him beg. that will teach him to ruin my mood a week before the trip.
21You weren't technically a couple and you hadn't had the talk so I would say go with him and get over it. I know I don't go into detail about everyone from my past so why should he if you weren't a couple.
22Agreeing with several others, I would makeup with him. The trip wouldn't have much bearing in my forgiveness or making up, but I'd enjoy the tan.
23get rid of him and either use the tickets with some one else or try and sell to someone.
24If you're not a couple how can you cheat?
25meh get rid of the guy... not worth the trouble... bring a girlfriend... you'll probably have more fun anyway tee hee
26I could never forgive anyone who cheats on me, I don't care if it's at the beginning or middle of a relationship. It's wrong, it's sh*tty, untrustworthy, etc.
I'd call it quits, no doubt.
27It happened before they were "official" so, he technically wasn't lying or hiding anything. What he did before they were official is really none of her business as far as his past lust life is concerned (as long as he's not infected with some sort of STD that he could have passed on to her). Maybe his last roll in the hay was the turning point at which he realized that he only wanted to be with her. If it were me, I wouldn't have wanted to know about it in the first place but now that I do, I think it's forgivable. As long as we have an amazing relationship and he's never "cheated" again, I'd still go on the vacation and put it behind me. No one is perfect, especially men!
28This has happened to me, minus the trip for the anniversey. I think if you asked him about this before and he lied about it, then the trip needs to be canceled and you need to really have a serious chat. If you never asked about it, and now all this new 411 is coming out, you just need to sit down and discuss it like two grown people who care for one another.
29For me, my thing was I just felt really hurt because I thought/wanted to be so amazing in my new guys eyes that he would even want to keep dating other women, even when we were not "boyfriend/ girlfriend". The thing is in the end, its not cheating if you all are not together. If he is generally sorry, I would forgive him, and use the trip to help recement any trust issues you have.
HOWEVER, BEFORE YOU GO----really talk about everything, how you feel, what happened. Don't drag things out. Ask your questions then and there, cry if you need to cry, get mad if thats what it takes. Then realise that he didn't need to even tell you in the first place and the fact that he did probably means he really does care.
i would still go on the vacation but would probably need some time apart from him for a few days before to kind of collect myself. if its before the 'defining' convo then its not cheating but if i wasn't seeing anyone and he still was then i'd def. be hurt. i'd also want him to come clean about anything else and tell him that if he doesnt do it now and it comes out later it will be it.
30"Of course, you're devastated, and you break up with him".
I have trouble with that sentence because I would not be devastated nor would I break up with him. He was with someone else when we were first *dating*, which is always a tricky stage. I wouldn't have issues with that piece of information, and I'd take the trip as planned. A year with someone is worth celebrating.
31I can't really get into this one, because I'm not grasping why one would be upset to find out that their boyfriend was seeing other people before they were exclusive...?
32HOLY CRAP!! This pretty much happened to me, just not quite as extreme. My bf cheated on me early on, except we actually were official, and I found out a little while ago, and we have now been together for a year. Also, when I found out he cheated, I was supposed to be going to visit him and go to a football game with him the next weekend. Goodness Dear, you hit that nail on the head, lol.
33We talked for days on the phone, and I ended up going ahead with my visit, and we talked about everything a lot then, and fixed some things and decided to work through it. So we have now been together for a year and 5 days, lol, and everything is getting better. It would depend on the circumstances of the cheating about whether I went ahead with the trip or not. I probably wouldn't go on the trip, that would only cause more problems with the two of you being stuck together and not able to get away and think, and I would feel like we were supposed to be romantic but of course we wouldn't be and it would just ruin everything for me. Also, even if it was before the two were an official couple, he probably knew he was doing something a little shady, because most girls (at least in my experience) aren't ok with guys doing that even if they aren't official, even if the guy was officially correct because they weren't "official".
The whole last part of my first post, from where I said: "Also, even if it was before the two were an official couple, and then all the way to the bottom, what I really meant was the same thing as what lilwildone1202 said, except she just worded it much better than me.
The guy wasn't really cheating, but if I was just dating him, it would still hurt.
34Before we were official? I'd go on the vacation. Yes, I'd probably be a little upset at first, but it did happen before we were official, so I don't think I could really be too upset about it.
35I'd still go on the vacation, but agree with lilwildone that I would want time for reflection prior to going. And I'd want a lot of back massages. And foot massages. And just overall pampering. A Lot.
36If the cost are split. Pay him for his half and take a friend or ask him to pay me my half and he should take his girl..
37I'd still go and make the most out of the trip. He admitted the "cheating" (which is a major plus in the first place!) and it was early in the dating stage. I'd give him a guilt trip for awhile and make sure it absolutely never happened again.
38I'd still go on the trip. It would be perfect to just work everything out. Plus he cheated so long ago and hasn't done it since. It was a long time ago and the relationship was not even official yet. That's hardly even really cheating. In fact the problem would be solved in the remaining days before the trip if I were in this situation.
39For me, cheating is a deal breaker. I don't like lying and if this happened in the very beginning during the get to know you stage, then he wasn't honest at all and I question all that he's ever said since then. I'd break up with him because chances are the trust has been severely compromised. Why bring it up now if he thought it was a non issue back then? In my opinion, he's getting ready for a change. Either he'll cheat again or he's looking to break up. At such a milestone moment in your life together why would he plant the seed in your mind of him with someone else??? I say go away with a very close girlfriend and enjoy your way through the sadness and pain. But definitely dump him. Then take what you learned from this into the next relationship you have. Oh, and by the way...don't offer to give him a refund on the trip. It should be his loss all the way around!
40i would postpone the trip...with most reservations you can move the date without a penalty (i'm a hospitality professional--there's always a way around policies) if i was in a relationship with someone and loved them and found this out, it would hurt. but....there is a time in the beginnings of new relationships where you are not an "official" couple. it is never fun to think about someone you love sleeping with someone else----even their past relationships, but it is true. it is unfair to think that you are the only person your partner has ever been with.
a situation like this would be tough, but i think if you loved someone you would want to work it out. i would do it at home instead of taking the risk of having a horrible time. then when we are better, i would go and have a fabulous time.
41Not a couple?
Not cheating.
It sucks - it was the beginning of the emotional attachment - but it wasn't infidelity. Take the cruise and renew the bond!
As an aside, I personally think he shouldn't have ever confessed. If he is really in love, it was in the past and it didn't matter. Some things are just better left in the closet... it only hurts the relationship.
42I would dump him and buy out his part of the vacation so I could take my best friend for some R&R.
43LMAO tell him to give the girl a call and take her.
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