DEAR HARRIETTE: I have recently befriended a lovely group of women who are slightly older than me — and exponentially wealthier.
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We met naturally and have struck up a lovely friendship, but the truth is they are way out of my league, financially.
They are all talking about taking a trip together this winter and have invited me to come along. I can’t imagine that I can afford it, but I want to try. I was told that once we get to the destination, there are few additional expenses.
Do I tell anyone there that I can’t hang the way they do? I’m worried I will be getting in too deep and won’t be able to afford to be their friend.
— Off-Balance
DEAR OFF-BALANCE: Who is your closest confidant in the group? Let that person know that you appreciate being included and want to be able to go on the trip with them, but you do have limited resources.
Ask what the expectation would be for expenses during the trip. This may feel awkward, but it’s way better to learn now than to be away and unable to participate or contribute fully.
If this is a group with whom you are supposed to be friends, there will be enough awareness of your circumstances that they will be inclusive. You will quickly learn how much you can or cannot do with them.
DEAR HARRIETTE: My boyfriend and I have been dating for almost a year now, and for the most part, things have been going really well. He’s kind and supportive, and he makes me feel valued.
There’s one thing that’s been bothering me more and more lately: how often he talks about his ex.
He brings her up in casual conversation, shares stories from when they were together and still texts and hangs out with her occasionally. He insists they’re just really good friends and that there’s nothing romantic between them anymore.
I want to trust my boyfriend, and I don’t want to be the kind of person who tells someone who they can or can’t be friends with, but at the same time, I feel this constant unease.
I don’t know if it’s a gut feeling or just my insecurities getting the best of me. I’ve mentioned it a few times, but he brushes it off and tells me I’m overthinking things.
Is it unfair for me to feel uncomfortable? How do I tell the difference between a legitimate concern and my own insecurity? Is it possible to set boundaries here without sounding controlling or jealous?
— Competing With Ex
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DEAR COMPETING WITH EX: Tell your boyfriend you would like to meet his ex-girlfriend. Explain that if he is set on having her be a part of his life, you need to know her, too.
Be open-minded when you meet. Genuinely look to see what kind of person she is and what quality of relationship they have.
You cannot control whether he keeps her in his life; you can evaluate what you see and decide if you can live with that fact.
Harriette Cole is a lifestylist and founder of DREAMLEAPERS, an initiative to help people access and activate their dreams. You can send questions to [email protected] or c/o Andrews McMeel Syndication, 1130 Walnut St., Kansas City, MO 64106.