Boyfriend going on trip with two women

Dear Guys,

So my boyfriend and I were together for 4 and a half years, broke up, and are now back together, going on strong for almost a year again now.

He is going on a trip with two female friends–one of which I am pretty sure has a thing for him–to one of my bucket-list cities, New York, during my FAVORITE time of the year, Christmas. I 1000% trust him not to cheat, but this bothers me a lot. Not only that it’s with girls, but the fact that he knows how much I want to do this and he isn’t even acknowledging my feelings, and he does NOT want me to tag along. Am I wrong to be upset? Am I over-exaggerating?

Obviously I am not going to stop him, as he would hate me for it, but I just need to know if other people have gone through this, if I am being crazy, and maybe how this looks from a guy’s perspective.


Dear Nicole,

How does it look? Well, to be frank, it’s not an ideal situation. And for the reasons you cite.

Look, we know you trust him NOT to cheat on you, but this is absolutely a trust issue. No, we don’t think he’s going to cheat, otherwise he wouldn’t be so open about his plans. However, we’re talking trust at the base level, the kind of trust that couples need in order thrive and endure, the kind of trust that says, “I’ve got your back and I know you’ve got mine.”

It’s not that guys shouldn’t have female friends—actually we encourage friendship across gender lines for many reasons. However, when you’re in a committed relationship decisions are not made in a vacuum. Every decision, not only affects the person making it, but their partner. The issue here is that he’s not considering you in this decision. He’s going on this trip whether you like or not, almost as if it’s a test to see what you’ll do, or how you’ll react. Have you talked about it with him? Have you expressed your opinion? What does he say? How does he respond? What if you put your foot down, would he go anyway? Would he break up with you?

So tell us about his relationship with these women? How long has he known them? Are they long-time friends? Is there a reason he might go on a trip with these women to NYC that we’re not seeing? (Work related? Other?) It almost doesn’t matter, but there could be extenuating circumstances that might make this more palatable.

In general, we’re not on board with his plans. We’ll give you a concrete example. Men and women can absolutely be friends with one another, even while one or both are in serious relationships, even married. That said, there are certain unspoken boundaries that shouldn’t be crossed. Going out for coffee or lunch is fine, but dinner might be crossing the line. What do we mean? The line is about perception. No, we don’t think you should make decisions based on what other people think, but in this sort of murky water, it’s a good indication of what might be “right” or “wrong.” If you went out to dinner with a guy friend, the perception by others would be that it’s a date. Whereas lunch or coffee might be interpreted differently. Going on a long trip with a female friend is dinner times ten, which is absolutely crossing the line. And think about it. What if the roles were reversed? How might he be handling this?

So what do you do? This is not necessarily a deal breaker. And we agree with you. You shouldn’t tell him not to go. (He has to come to that conclusion on his own.) But we do think a heart-to-heart is in order. Either before or after. Obviously, you’re upset, and that feeling isn’t going to go away. However, do your best to talk with him when you’re not feeling too emotional. That could cloud what you’re trying to say, and he could focus on your emotions rather than the issue at hand.

Finally, you need to ask yourself what kind of partner you want. Do you want someone who’s going to make decisions in a vacuum or someone who is going to consider you when he makes decisions? Remember, life is long, and if he’s doing this now, this could become a pattern.

We hope it works out for you.

Take care,


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11 Comments on Boyfriend going on trip with two women

  1. Hi Guys,
    I am a single mum with two children (9 and 11).
    I have been separated for 14 months and have started talking to a guy I met online since April this year.
    He has 2 children (12 and 19) and he resides in Queensland, Australia while I reside in Victoria, Australia.
    He is 9 years older than me, which doesn’t bother me as I find that I relate more to someone older than me.
    I have since moved to Queensland (not because of him, but for support of family and friends) in the last 2 weeks.
    He has travelled to Melbourne to see me in June this year and I have spent time with him in Queensland in August this year whilst researching schools in the area.
    Throughout the months we have always kept in touch and continually speak, text, etc to “check in” and say hello.
    When I was in Queensland for 3 nights I stayed on my own, but two doors down from his apartment as he had his younger daughter staying with him (completely understand as I would have done the same). He did, however, invite me to spend time with this daughter and head out to dinner and then come back to his house to watch tv, invite me to a family birthday and introduce me to his older daughter also.
    He did not show any affection during that time as he was worried about his daughters reaction (again, understandable), nor did he show any affection whilst with his family, but introduced me as a “friend who was moving up here from Melbourne”.
    Since moving up here we have had a “straight forward” chat and he has said that he has been with someone else (even told me her name) but he doesn’t feel that she is the one for him.
    We spoke, mutually,!about getting to know one another “behind the scenes” and also doing things together with the kids, in order for them to get to know each other, but acting purely as friends when the kids are around (which I totally agree with) for 4-6 months.
    He also says that she knows about me as the friend that moved here, but doesn’t know that I’m with him.
    We recently went out together for an after school treat so the kids could meet each other and my kids meet him, which turned out great.
    Things are looking fantastic, but my question is – is he serious? He is the most beautiful man and will do anything to help me…he’s even spoken about getting a surfboard for my son for Christmas as he is learning to surf.
    He has also said in conversation that, having gone through the divorce that he has, the next person he wants to “be with completely” is the last person.
    He also said that he “really likes me”, and we even spoke about love to which I replied that it will be quite a while before I fall in love again.
    Babies also came up briefly in the conversation – he asked if I would want any more. I said that I am happy where I am to which he replied “so am I, but if the person I end up with wanted one I couldn’t say no”.
    I haven’t been on the dating page for over 17 years and would love some kind of clarification from a guys perspective.
    Thanks in advance 🙂

  2. @Kitts……Honestly, your situation seems like it warrants a longer, more in-depth conversation. We’ll try, but we don’t think we can do it justice here in the comments section. (We’d recommend that Ask a Private Question option on our site. Yes, there is a fee, so read the testimonials to see what clients say about us.) That said, how did he react to your moving to his home town? Was he happy about it? Or was he mixed? Are the two of you intimate or just friends? (Let us know if you’d like to continue here, or privately via email) Remember, this is a public forum and we don’t delete comments AFTER the conversation. Thanks. And take care.

  3. Thanks so much for returning my email.
    He was genuinely happy when I told him that we were moving and had said that he honestly didn’t think that I was going to make it up here (due to having to get permission from the children’s father).
    My children and I had flown up and by the time I was off the plane in QLD I already had one message saying have a good flight and speak to you when you arrive to which he rang 5 minutes later.
    We are intimate, but only when the children are not around and he always has a smile on his face when he sees me, as I do when I see him.
    We have also spoken about his mother who is staying in QLD for a year, saying that she would “drive me insane” and he has also met my mother who was over here helping me with the move.
    Thanks so much for your input and I look forward to hearing from you 🙂

  4. @Kim….It seems like the two of you really care for one another, and we think you’re handling the complex situation with your children very well. (Both of you) In general the two of you seem to be on the same page. All good. However, then why did he feel the need to be intimate with this other woman?

  5. I see your point.
    He has been with her for a while now – he has said that she always offers to look after his younger daughter. They are parents from school and he said that he didn’t intend for it to happen but it did and they then became fwb.
    When he needs a partner for something he takes her.
    I”m hoping now that I”m here that this will change in the near future.
    He has also said that after 4-6 months of letting our children get to know one another as well as ourselves and when we both feel comfortable that the children would be fine with us being “together”, he will then tell the otter lady about us and stop their relationship.
    For the children’s sake (both of ours), I agree witth what he is saying, but I also believe that he perhaps doesn’t want to lose the other lady yet, even though she “is not for him” as they are also friends through their children.
    He came over late the other night and we “caught up”. Afterwards we had a great conversation about his older daughter and how her study, etc is going, as well as our younger children and how they are doing in school.
    He is opening up to me about family and parts of his life which leads me to believe that there really is perhaps something there…as a fwb, I really don’t think he would be letting me into his world and he certainly wouldn’t be interested in mine.
    Am I thinking right or am I perhaps in my own little world at the moment?
    Thanks guys and I look forward to hearing from you 🙂

  6. @Kim…..Questions before we give our response: Are the two of you currently intimate? Or have you been? Is there any sort of passion between the two of you or is it more like friends?

  7. Hi Guys,
    Yes, we are currently intimate. There is a little passion there, yes.
    I have since found out that he is moving in with his other fwb as he says it works well financially – when I questioned him about it he advised that he “has to do what’s right for him and financially it will be better for him until he becomes more stable in his life again”.
    When I questioned him as to how we would get to know one another as well as the kids when he is living with her he advised that they would barely see each other because of their work hours and that when he sees her he doesn’t always want to “f@ck” her, but when he sees me he feels that he just wants to “f@ck”.
    After we were “together” we spent the day together – although it was at his place, and he fell asleep on the couch with me stroking his back.
    He said he understood if this was not for me but would be a little hurt if I wasn’t around.
    In another conversation he was telling me about his friend and how he has come out of a messy divorce, that he is the nicest guy, etc. he said that perhaps if I were introduced to him that the four of us (him with his other fwb) could go out to dinner and then I could meet his other fwb.
    I said that if this guy was his friend then why would you want to see him hurt again and he said “I know it’s a little manipulative, but this way we get to spend time together and I get to have you whenever I want”.
    I am not this type of person and also advised that I do not want to hurt anyone who has been extremely hurt before.
    He also said that he doesn’t know me yet, but also doesn’t know how things will end up with the other fwb.
    I also asked him if his family knew what was going on with him and I and he said he had spoken to his sister about it (who I have met) and she said to do what makes him happy.
    I also saw an email briefly on his laptop which was opened from another dating site.
    In light if all of this new information I think I now now the answer to my original question…is he serious?
    In your opinion, should I be pulling away or see how things pan out as he is also fulfilling my needs. I just don’t want to get hurt again.
    I look forward to hearing from you.

  8. One more thing – he’s still talking about getting my kids something for Christmas…I don’t understand this – is it just to keep me around or is it genuine?

  9. @Kitts……We think you know the answer. In our opinion, he’s got a lot of nerve, and you seem to be going along with it. Just because he’s being open about things doesn’t mean what he’s doing is okay. Think about it. He’s basically moving in with another woman. He cites financial reasons, but of course he sleeps with her too. Sounds like a cushy situation for him. (But it doesn’t speak well to his morals.) And what about her? How does she feel about it all? Has he told her about you? It seems like he’s getting everything he wants—two women to have sex with, plus help with his finances. We’re sorry if we’re being too harsh but it’s important for us to be honest. And we are trying to be supportive of you. We don’t think this is a great situation for you and it’s not going to improve any time soon. And ask yourself: Is this the kind of guy you want to be with? Sure, he probably has some good qualities, but he’s definitely only looking out for himself.

  10. I agree – everything you say has definitely “hit the nail on the head”.
    As difficult as it may be, my best option, and the best for my children, is to pull away.
    He says that he has told the other fwb that we have had a basic lunch together at a cafe, but he hasn’t told her that I have been to his place.
    My personal downfall is that I am too nice and too caring – perhaps I need a tad of “attitude” lol.

  11. @Kitts……A little attitude might be good! 🙂 But being nice is good too. Balance, balance, balance. Be well.

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