A
female
age
41-50,
anonymous
writes:My boyfriend of a few months has a female best friend, Sally (pseudonym), that he used to hook up with intermittently but never formally dated. Sally moved to a different state for school and he ended up following her out here a year ago to find a job. I started dating my boyfriend when Sally went to study abroad for the summer, but she will be back soon. Sally is the type of girl that just hooks up with random men and doesn't want a relationship or to ever get married. I know very little about the exact nature of their past relationship, but I fear that my boyfriend has unrequited feelings for her. He told me that he hasn't hooked up with her since he moved here 1 year ago, but that doesn't include sleeping in the same bed, cuddling, etc. In fact, when he moved here, he was living with her. I've been so uncomfortable and nervous about getting involved with him now (I've been cheated on in the past) that I went into his email and searched the key terms "Sally" and "hook up". I did find an email from about 14 months ago... What I found didn't tell me that they definitely hooked up, but she did offer to have sex with him when she returned from a summer vacation (this was 2009)...and even mentioned the possibility of still hooking up at least just once even if he had found another girlfriend by then (The nerve!). His response was vague but flirtatious. I did try to talk to him about my discomfort and said I was having a hard time trusting him. He repeated he hadn't hooked up with her since he moved here and that we wouldn't work if I don't trust him. He said he doesn't sleep with multiple people at the same time and we have agreed to be exclusive. I know I have some past relationship baggage from being cheated on, but I have a lot of conflicting feelings now. I'm even looking in his inbox to see how they talk to each other while she is studying abroad again this summer (which I hate that I do, but can't help it!). He calls her beautiful, signs his name with Love, says he misses her. I have a feeling I'm going to have some difficulty dealing with jealousy and I don't want to expose myself to STDs if they do secretly hook up. Also, I fear I will have difficulty coping with him sharing an emotionally intimate relationship with another woman because he shows difficulty sharing his feelings/thoughts with me, like many men stereotypically do. If I wasn't so attracted to him, I probably wouldn't put up with the possibility that I may be 2nd in importance to him. I'm not going to make him choose between us because I'd rather just leave the relationship than do that. Kind and helpful opinions are appreciated more than sarcastic remarks. Thanks : )
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best friend, flirt, jealous, std Reply to this Question
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Fancy yourself as an agony aunt? Add your answer to this question! A
female
reader, QuestionsInLife +, writes (13 August 2010):
You were wrong to snoop through his emails, and it shows that you have a lack of trust. But on that note I think your boyfriend is in a precarious position. Often times FWB often hook up together because "it's just sex" and obviously the other woman doesn't care if he's dating someone else.
I'd recommend that you stop the relationship because you are jealous and don't trust him. These situations often deteriorate and at the end of it you'll be scratching your head as to why you stayed.
One of my bfs "hooked" up with a former FWB and told me that because he didn't have feelings for her, it didn't matter. But your fellow still seems to care for her. Whether you stay or go, it's your decision. But I'd recommend condoms every time unless you want to catch something.
A
female
reader, chigirl  +, writes (14 July 2010):
 You need to trust your man. Having a friendship with someone you've had a sexual relationship with does NOT invite to cheating anymore than any friendship invites to cheating. If your man is is loyal and trustworthy then there is no problem other than your own insecurities. This woman is not a threat to your relationship unless your man allows her to be, and if that was the case then you would not be able to trust your man around any woman as he could be cheating with them too.
FWB or not, you need to trust your man. But on the other hand: trust your gut feelings. If you have suspicions that theirs relationship is still continuing behind your back, rather leave the man than walk around being constantly scared of what might be going on. If he treats her like he wants her and loves her, maybe it is time to find someone 100% dedicated to YOU. It's only been some months, you have not wasted too much time yet. But, don't confuse a good friendship with sexual attraction, and don't confuse "you are beautiful" with "I want to cheat on my girlfriend with you".
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A
female
reader, SillyB +, writes (14 July 2010):
 You are being too relaxed about this.1. Your boyfriend should not be friends with someone he's slept with. Its not respectful towards you and it just opens the door for cheating.2. He has trouble being open with you. Thats a red flag. Why be with a man you cannot share thoughts/plans/ideas/aspirations with? You want to be with someone that is your 'bestfriend'. Who shares everything with you. Apparently, he already has a best friend, so why be second place?3. Wear condoms with him4.He shouldn't be telling her in emails she is beautiful and that he misses her. HUGE red flag. He has feelings for her. I would be very upset over this too.As a female there is NOTHING wrong with speaking up and getting upset. I would nip this in the butt right away - he shouldn't be in contact with her as long as he wants to date you. YOU should be his best friend!! If he is not in agreement, please walk away. You're young and there are plenty of guys that would be interested in you!
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A
male
reader, dirtball +, writes (14 July 2010):
 I apologize, but I have a feeling this may sound harsh. You should NOT be digging through his emails. What a horrid thing to do. You're holding something against him that you found from almost a year before you were together. What this tells me is that you're not ready for a relationship. The issues you have with being cheated on in the past are still ruling your life, and likely will until you can get a grip on them.
To clarify, I don't think that the way he is addressing her is right either. I only sign "Love, Dirtball" to family or my GF. However, your 3 month old relationship is a blink to the time he's known this friend. I may have flirty conversations with friends too, but that doesn't mean I'll act on them.
So, to summarize my view of this situation:
- You have major jealosy and trust issues to work out before you can have a meaningful romantic relationship with anyone.
- Your BF has unrequited feelings for this girl or he wouldn't have moved to follow her.
- She strings him along because she likes the attention she gets from him, and they likely do have a good friendship on some level.
- You've already doomed this relationship with your snooping and mistrust. Get out before either of you gets any more attached.
Again, this isn't meant to be mean, but I'd drop you in a second if I found out you were going through my emails. That would tell me very clearly that you don't trust me at all. At that point I would GTFO. Trust is a two way street, and while he hasn't earned yours yet, if I were him, you would have destroyed mine.
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A
reader, anonymous, writes (14 July 2010): If you are going to be with him, you just have to except the fact, he also enjoys other women
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A
female
reader, xanthic +, writes (14 July 2010):
 If he's really speaking to her that way, I think you should be concerned. He most likely does still have feelings for her, and it's up to you to decide if you can trust him to be alone with her knowing this.
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