Dear Wendy: “I Think I’m In Love With My Best Friend”

It’s time again for “Shortcuts.” For every question, I’ll give my advice in three sentences or less, because sometimes the answer to a person’s question is so obvious and the need to hear it so great, being as clear and frank as possible is simply the best way to go. Today we discuss falling for your best friend, breaking up with frenemies, and when to butt out and stop giving advice.

I think I’m in love with my best guy friend. We went to college together for a year and we became very close friends. We always had a flirty friendship, but neither of us ever made a move. He moved across the world recently for grad school and I haven’t seen him in about four months. However, we talk multiple times a day and though our conversation seems pretty innocent, he tells me he misses me and he wishes he could come visit. I am going to Europe soon which is not close to where he is, but it’s closer than the U.S. He has been jokingly checking on tickets to come visit me while I’m there. But I’m confused by him. He has never said anything about being more than friends but I’m the only woman in his life (that I know of) that he talks to so much and says these kinds of things to. We are both single and I think I’m in love with him despite the distance. What should I do? I can’t keep living with this confusion. — Oceans Apart

The next time you talk on the phone tell him that you aren’t sure if it’s because he’s so far away and the distance fuzzes things a bit, but lately you can’t help wondering if there might be potential for something more than just friendship between you. The whole “distance fuzzes things a bit” line gives you an out if he doesn’t feel the same way, but if he does, then invite him to come visit you when you’re in Europe and see what happens when you get some face-to-face time.

My girlfriend and I have been dating for almost three years. Last September, I moved half a continent away to finish my bachelor’s degree. The first six months were easy for me and difficult for her. The past six months have gone the other way around. I’ve gotten rid of my Facebook account because I can’t stand to see pictures from her nights out with friends. I have no problem with her going out and having fun, but I feel like it’s a slap in the face when she tells me to check out the pictures from her night out last week. Especially because none of the things I see in the pictures seem anything like how she acts with me. When we used to go to the bar it was a beer or two and then home early. With her friends it’s shots and dancing and hugs with guys I don’t know and they don’t leave until they’re forced to. What is going on? Am I being too sensitive or is there a reason why she seems to relish her solo partying over when we used to go out together? — Mr. Missing Out

So … you say you have “no problem with her going out and having fun,” but it’s a “slap in the face” when you see evidence of her having a good time with friends and not going home early like she did when you were around? I hope before you return home, your girlfriend realizes what an insensitive, selfish, controlling bore you are and how much more fun she has without you. And I hope you realize the reason your girlfriend “relishes her solo partying” is because she isn’t some pathetic chick whose life revolves solely her long-distance boyfriend.

I have a friend whom I don’t really like any more. She has a good heart, we have a lot in common, and our friendship started out well, but more often than not she is just kind of a bitch to me … she is extremely judgmental, very non-supportive when I need support — yet she expects endless support over tiny little things — and she criticizes me, etc. My husband calls it my “abusive relationship.” I’ve had a few friends like this in my lifetime, and I’ve never known what to do about them. I don’t know how to “break up” with a friend. Further complicating the matter is the fact that we see each other EVERY day because we are attending the same professional school. We have many mutual friends; however, most of them feel similarly about her as I do. I don’t want to hurt her, or have it be awkward, but I hate being friends with her now. What should I do? — Sick of my Frenemy

Since you see each other every day and don’t want things to be awkward, a cold-cut breakup would be inappropriate. Instead, do the “friendship fade-out”: gradually stop inviting her to do things with you; quit returning her texts/emails/and phone calls; avoid one-on-one time with her; and when she invites you to do something, “have plans” about 75 percent of the time. If she asks you what’s going on, tell her you’ve just been really “busy.”

My sister and her husband had a very brief courtship and were married after less than a year of dating, got pregnant after three months of marriage, and now have a 1-year-old son. About two years ago my sister asked me to give her free advice and financial planning assistance (what I do professionally) to get them off to a good start in their life together. After all this time, they have made very little progress. Her husband has basically told her to take care of their finances — that he makes “plenty” of money (both of them work full time to pay their bills). While she tries desperately to get ahead and start saving for a house and for their son’s college, he continues to spend frivolously with no regard for their financial situation. She calls me at least once a day to ask for my advice and help. I have tried to explain to her that they need to decrease their frivolous spending in order to meet their savings goals (a concept which I think is pretty simple) but she doesn’t seem to understand the “THEY” part, and won’t confront her husband about his spending because she doesn’t want to fight with him. Her husband has been getting the message about my insistence that he change, however, because he has started to voice his resentment about my involvement in their finances, saying she should lie to me about his excess spending (specifically his adding $4,000 to their debt in one day). To top things off, my fiancé, whom I have been with for more than four years, has been getting increasingly frustrated with the amount of time I spend helping my sister when, to him, it isn’t helping. How can I help my sister understand that the problems in her relationship are not about money, but about communication (or rather a lack of), and how do I preserve my relationship and distance myself from their issues without cutting off my family? — Financial Planning Sister

Good lord, FPS, if you’ve been giving your sister advice “at least once a day” for two years and things aren’t any better for her, it’s probably safe to assume you can’t help her. So let her deal with her own mess, and focus on your relationship with your fiancé before you screw that up. The next time your sister calls for help, tell her you want to go back to being her sibling and not her financial planner and that if she still wants financial advice, you can refer her to one of your colleagues.

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