Hey Guys,

I’ve been with my first very serious boyfriend for a year and a half now, we have a seven year age difference. I’m 23, and he’s 30. He is a divorced and has a child from his first marriage. I love him dearly and have accepted him and moved on from the baggage issue. His family knows about us; however the problem is that his older sister, whom I have not yet met, seems to not know.

While snooping through his email—which I know is wrong and a breach of privacy—I realized that in an email to the sister he had sent her a list of items to bring from overseas. (Things for his son, himself, me, and the ex wife.) My issue is, what he ordered for me (two pairs of shoes) he listed under the EX’s name! His ex knows about us too, but I am hurt that he would not acknowledge me to his sister. I’m hurt that these very petty things keep coming up at this stage of the relationship. I’m hurt that he has pretended that my stuff is what his ex has asked for. (The fact he is still getting her things is another issue on its own). I don’t know what his behavior means and don’t know how to approach it without spilling the beans on my spying. As I said, he is my first real love, he is the first guy I’ve been intimate with and I’m not prepared to leave him. I want this to work but for everyone to know who I am. Please help!



Dear Stephanie,

Thanks for your question. Clearly you’re looking for more reassurance from your boyfriend that he’s as serious about the relationship as you are. And we understand that it would be validating for you, if your boyfriend told his older sister about your relationship; but it doesn’t mean the opposite just because he hasn’t yet. (Maybe he’s waiting to tell her face-to-face? And he doesn’t want to have to explain in an email or via phone.)

But let’s talk about your snooping. Why were you snooping in the first place? What gave you cause to mistrust your boyfriend? And is this something you do on a regular basis? If so, why? It seems to us that you’re feeling insecure in this relationship and we’re wondering where that’s coming from. You, him, a specific event, or some combination? Because you’re right, if you had no good reason to snoop—meaning, you didn’t suspect him of cheating—there’s no way you can admit to doing it. Something to think about. Please enlighten us. (This process may help you as well.)

We agree with you that he seems a bit too emotionally connected to his ex. Sure, they need to have an amicable relationship in order to raise their son in the healthiest environment, but ordering her items from Europe seems a bit over the top. (Of course if they are friends—which is actually better than being enemies; for you as well—then this is what friends might do for each other.) That said, sometimes it’s necessary to put up clear boundaries in order for each spouse to move on and rebuild their lives. It’s not fair to their present partners either. (Meaning, you)

Some of your insecurity Stephanie, probably stems from two sources: Your age difference and stage-of-life difference. The fact that he’s already been married, has a child, has an ex-wife, has been working for a while, possibly makes you feel like he has a step up on you. It doesn’t need to, but that’s pretty typical, and that’s why it requires even more trust and communication to make these types of relationships work. He needs to reassure you that he indeed is very serious about you and doesn’t feel above you and you need to let go of some of these worries and trust that he loves you. Otherwise you’re going to be in for more confusion, resentment, and heartache as this relationship progresses.

Stephanie, if you’re constantly feeling inadequate, unsure, worried, suspicious, and upset, on a regular basis, that’s something you need to consider. We’re not saying this relationship can’t work, but sometimes if a relationship is a constant struggle, it’s just not worth it. Hopefully it won’t come to that.

So you need to start talking to him more about some of your fears. Try not to overwhelm him—he’s got a lot on his plate already—but he does need to know that you’re feeling uneasy about things. (It doesn’t even have to be specifics.) But remember, since he’s at a different stage of life, he may be looking for a relationship that’s easy. And if this gets too complicated for him, he might bail. And this is what we mean. Just be careful not to compromise everything you want out of a relationship to be with this man. Seriously. He’s got a major head start on you. If he’s willing to slow down and work with you so you’re both on the same page moving forward great; but if he’s not, that’s something you really need to think long and hard about. Either way we wish you the best and hope this gives you some perspective.

We’d love hear your thoughts on this and get some answer to our questions so we can offer a few more opinions. (If you want more!?) Also, feel free to ask as many follow-up questions as you’d like.

Take care,


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