Dear Bossip: I Was Paying For Everything, Now He Works & I Still Pay

- By Bossip Staff


Dear Gay Best Friend,

About 6 months ago I met two men and dated both only a couple of times before I decided who to continue seeing.

At the beginning of this relationship my current boyfriend lost his job so I started paying every time we went out for dinner, movies, drinks, etc.  Fast forward 6 months, he has a job but I still continue to pay every time we go out.  He doesn’t even make an attempt to pay and goes as far as to hand me the bill when the waiter gives it to him!!!

I also just found out that he is talking and texting an ex-girlfriend that he dated for 5 years.  I found out because I saw a text message from her saying she “misses him so much.”  He said he is not seeing her (she lives 2 hours away) but made it very clear that he plans on continuing this friendship with her despite how I feel about it.  I don’t know how he feels about me or where this relationship is going because he is the kind of guy that doesn’t express his feelings.

The other man I met at the same time 6 months earlier has reappeared in my life.  He wants to start dating and says he wants to get it right this time.  The reason I didn’t choose him in the beginning is because he lives 1 ½ hours away from me, and I don’t do long distance relationships very well.  I have tried them before and got burned so I have trust issues with that.

My question is do I stay in the relationship I’m currently in and believe him when he says he is not seeing her, start dating the long distance guy, or do I say deuces to both and start with someone new altogether?

Just so you know I have been divorced 15 years so I’m not afraid of being alone or starting over.  I just want to make sure I’m not getting in my own way with past baggage that makes me see things that aren’t there. LOL! Your honest opinion would be greatly appreciated. – Sitting in Limbo

Dear Ms. Sitting in Limbo,

Girl, get rid of them both!!! The hell is wrong with you paying for dates, dinner, drinks, and movies with a man who has a job, earns money, and should at least make an attempt to take you out and pay? This man has the audacity to hand you the bill when the waiter shows gives it to him. Though the action is sexist for a waiter to assume the man is paying and giving him the bill, nonetheless, your man doesn’t even think twice about handing it to you. Put that –ish on ice tuhday!!!

Chile, ain’t no d**k that good that you need to be paying for it! Is he your gigolo? Are you his sugar momma? The hell is wrong with you women dishing out cash for men! Is this the new thing in 2013 where you women are allowing yourselves to be used by men in return for companionship and sex?

Your man is a bum. He’s mooching off you and taking advantage of the situation. I personally don’t understand why you were carrying him and paying for everything from the beginning, anyway? Why date a man who doesn’t have a job, and six months later he is still jobless? Where was he living? Who was feeding him before you came along? And, you mean to tell me that between the two men you purposely chose the one who had no job and you had to pay for everything? Chile, the thirst is heavy and women are clueless and running rampart with d**k-matizitis! LOL!

That is one situation you should have never got yourself into because once you set the precedent of how the relationship starts, it will continue down that path and it’s hard to break that pattern.

You trained your man into thinking you would always take care of everything. And, you did. You trained him to believe that you were the money bags of the relationship, his sugar momma, and he continues to treat you as such. Therefore, he won’t be a man and take responsibility or accountability for his role in your relationship. You have trained him on how to treat you, and you allow it.

Then this MoFo has the nerve to tell you that he is going to communicate, and maintain his friendship with his ex-girlfriend regardless of what you think. No ma’am! You should have put that man right together!!! You are his present, and his ex is his past. If he is interested in your relationship and building something with you, then he should respect your feelings and the boundaries of your relationship. If you’re uncomfortable with him communicating with his ex and he tells you that he is not going to stop talking with her. Then, ask him how does he feel about you communicating and keeping in contact with your exes. His response will give you the answer you need to move on.

And, sweetie, the next time you’re out to dinner, make it the last supper! You get all dolled up, and smelling good, and go to your favorite expensive restaurant. You order drinks on top of drinks. Then, order the most expensive dish on the menu, and top it off with a lovely dessert. As the dinner comes to a close, you excuse yourself to go to the restroom, and instead you make a beeline straight for the front door and exit stage left! Leave his a** right there, and make it the last time you see him or communicate with him. Let his ex-girlfriend come bail his a** out since he wants to stay in contact with her.

In regards to the other man who reappeared and wants to make get it right this time, uhm, hell naws! If he couldn’t get it right the first go round, then there won’t be a second go round. And, you’ve expressed that you don’t do long distance relationships. If you don’t do them, then don’t start doing them. HELLO!!!

But, I’m a little baffled that you are deciding your relationship fate between two men whom are obviously not good for you. Those two men are not the only two men in the world, you know? There are a plethora of eligible, attractive, smart, hard-working, loving, capable and able men who would love to be in a monogamous relationship. Why are you deciding your fate between these two bum a** knuckleheads? You need to get out more and explore. The world is full of good men.

And, if you have no problem with being alone, and waiting, or starting over, then why don’t you do that? You don’t have to decide between these two undesirable choices. Why mull over these men? UGH!!! Honey, leave both of these men alone, and go do you, ALONE! I can’t believe that you are allowing yourself to be used by a man who has a job, and he’s made no attempts to repay you for all you’ve done for him, or at least take you on a vacation, cruise, or hell, buy you a card. This man basically is telling you to kiss his a**, and now it’s time for you to make him kiss yours as you walk out of his life! – Terrance Dean

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author terrance dean

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!

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