Dear Bossip: We’ve Been BFF’s For 8 Years, But I’m Wondering If We Should Cross The Line To Intimacy

- By Bossip Staff

Dear Bossip,

My best friend and I have known each other 8+ years (he is 31 years old, and I’m 29 years old). We met through a mutual acquaintance and later discovered that we attended the same school.

There was never a flirting relationship between us, just jokes and genuine dislike of “aggressive” people. We’re both laid back go with the flow type of people. Most likely, this is why our friendship only ever existed on campus, i.e., we never hung out in a different setting, other than the first time we met.

Fast forward 2-3 year, we’re both in relationships with other people. Mine ended; his turned into a marriage and a son. His wife was very controlling about him and our friendship. I’m not the type to step on anyone’s toes so her dislike of me made me remove myself from the situation. Thus, our friendship literally became nothing more than phone conversations here and there. I would talk to him like he was one of the girls and he would talk to me like I was one of the guys.

A year into their marriage his wife (24 years old at the time, with 4 kids that weren’t his, plus their 1, 5 total) began to go out, A LOT!!!! Also, his wife would have the car so on days that I could he would ask me for a ride home from work, which was no problem, but again that was our friendship. The only time that we would see each other was a 20-30 minute ride home from work. Eventually, his wife got herself a boyfriend and asked him to leave because he worked “too much” and didn’t give her the attention she required.

During this time our type of friendship didn’t really change. I would just listen to him as he questioned what he did wrong and how he could get his wife back and so on and so forth. At this point I myself was in a relationship and many of those conversations would be between the three of us. My ex telling him that he needed to get back out there (during their marriage he had lost friends and family by staying) find some friends and a new lady. Which he eventually did, but he’s not into dating. He’s a homebody and misses the family life.

Last October my boyfriend ended up leaving me to chase his dreams of being a rapper. Also, around that time I had lost my job, so when he left I was left with stacks of bills and nothing more than a part-time job. My best friend, however, had finally got the job that he wanted and things were and still are getting better for him and recently he has been my rock.

We’ve spent more time together in these last two months than we have our entire friendship. We go everywhere together, anything I need he provides, and if his ex goes nuts about the kids (her boyfriend left her, and he still takes care of her kids as if their his own) asking for more money leaving him broke. I do share the little that I have so he can eat, have gas money, etc. Also, we have never EVER crossed that friendship line, but…

Our families love each other and not one moment goes by without one of them telling us to cut the –ish, and get together. It’s gotten so bad that our mutual friend is even joining in on the act and saying that we should give it a try. I don’t know what he’s thinking, but for me I know that the both of us needs this friendship right now more than we need to take a chance. But, things have gotten so bad between us that we no longer date other people, we’d rather do things together.

Only time we’re with someone else is for sex, then when one tells the other its hints of anger on both sides, but neither of us go into detail. We both just shrug it off and down play the relationship we have with others. When I do ask him why he doesn’t date anymore he’ll say things like, “I’m tired from work” or “I don’t have the money right now,” but then he’ll turn around and ask me, “Where do you wanna go?” Or, “What are we gonna do today?” I’ve told him that I don’t want to cramp his style, but he’ll just ignore me or say “I’d rather be around you than them.”

At this point I don’t know what to do or think. Should I continue to go with the flow or is this turning into an unhealthy situation? – Crossing The Line With Bestie

Dear Ms. Crossing The Line With Bestie,

Misery loves company!

Yes, I do agree that this is an unhealthy situation. You are co-dependent on each other, and notice that you’re always together, especially when things are not going well in your relationships, or when you come out of relationships. You’ve become each other’s ear, and shoulder to cry on. You run to each other to be consoled, and to bish and complain about others, and what’s not working in your life. You’ve developed a relationship that is totally reliant upon each other’s misery. And, it’s not healthy.

Look, don’t you think when you met years ago when you were in college that he would have stepped to you and pursued a relationship if he was interested? And, don’t you think after all this time, at some point it would have dawned on him, he would have made a move and pushed up on you if he was really that interested? What I’m sensing is that you are more invested in his life, and what’s going on with him than he is with you.

But, I get it. You’re both emotionally and mentally needy people. And, he feeds your desires to be emotionally and mentally heard, and at the same time, you feed his desires to be emotionally and mentally heard. You feed off of one another. That is why he said that he would rather be around you than them. You understand him, get him, and support his emotional and mental rants. It’s baggage, and you both are carrying each other’s baggage. Other people don’t want to be bothered because it becomes draining. But, it feeds the both of you.

Think about your friendship, and notice the pattern between the two of you. When he needs something he runs to you. You asked him why isn’t he dating someone, and he said he’s tired from work, and he doesn’t have any money. Uhm, he doesn’t have money because he is giving his money to his ex-wife who left him, and he’s supporting her and her children that are not even his own. He has one child with her, but he is taking care of a household full of people. That doesn’t make any sense. So, why is he doing it? Why is he giving her all his money? And, why are you supporting him doing this, and why are you giving him money for food and gas?

But, this is the kicker, he turns around and asks you where are we going to go today, and what are we going to do today. Who’s paying for this? He doesn’t have the money, so are you supporting him and taking care of him? Why? Friend or no friend, he has to become better at managing his own finances, and stop acting like a damn child. He has to grow up and become more responsible. But, neither of you see what you’re doing. You two are doing nothing but using each other. Using each for emotional and mental support. Using each other for financial support. Using each other as shoulder’s to lean on and cry on, and mope and bish to.

You both need to be in therapy, and, in particularly he needs some serious therapy. You can’t fix him, help him, or solve his problems. But, he keeps running to you because you are the only one who will listen to him, and give him a stage to perform. You support this bull-ish, and he will keep using you, sucking your energy, and draining you. And, guess what, neither of you are in relationships, but he will find another woman, and continue this pattern with you.

No, I don’t feel you should cross the line with him by becoming intimate. It will only complicate your relationship by making it physical and sexual. You’re already emotionally and mentally in a relationship with him, and it has proven to be unhealthy, therefore, making it sexual will only make it worse. And, what happens once you discover you’re not physically attracted to one another, or the sex is awkward and contrived? Also, look at his pattern and behavior. Nothing will change between you and he. He will continue to work, take care of his other family, and complain about his life, and you will continue to support him, and be his sounding board.

Stop being his sounding board. Stop financing him. Stop being his co-dependent partner in these emotional and mental rants. Stop giving him that much access to you. Stop letting him use you. I bet if you stop doing these he will find someone else to drain and suck the energy and life out of, and he will miss you for not being there for him, and helping him, and listening to him. It will become about him, and not how he’s treating you, using you, and how he leaves you each and every time he comes and takes from you. It’s time for a reassessment of your friendship, and what you clearly are not seeing. – Terrance Dean

Hey Bossip Fam, what do you think? Share your opinions and thoughts below! Also, e-mail all your questions Terrance Follow Terrance Dean on Twitter: @terrancedean and “LIKE” Terrance Dean on Facebook, click  HERE!

Make sure to order my books Mogul: A Novel (Atria Books – June 2011; $15); Hiding In Hip Hop (Atria Books – June 2008); and Straight From Your Gay Best Friend – The Straight Up Truth About Relationships, Love, And Having A Fabulous Life (Agate/Bolden Books – November 2010; $15). They are available in bookstores everywhere, and on Amazon, click HERE!


Make sure to order my books Mogul: A Novel (Atria Books – June 2011; $15); Hiding In Hip Hop (Atria Books – June 2008); and Straight From Your Gay Best Friend – The Straight Up Truth About Relationships, Love, And Having A Fabulous Life (Agate/Bolden Books – November 2010; $15). They are available in bookstores everywhere, and on Amazon, click HERE! – See more at:

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