Dear Bossip: I’ve Been Talking To A Guy Who Has 3 Kids From A 14-Year Relationship & I’m A Little Leery

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Categories: Love and Relationships, News, Sex and Relationships

Black woman thinking

Dear Bossip,

I have known this guy “Jason” for about 2 years now and we have just been casual friends, having small talk when we run into each other in the neighborhood up until a few months ago.

We started texting and talking more gradually since the beginning of the summer and now we text each other ALL day and night. We haven’t had the chance to go out yet because we both have demanding freelance jobs that just never seem to have down time at the same time (I have had to cancel on him a few times as well) but we connect on an intellectual and spiritual level.  We haven’t been intimate yet but the attraction is definitely there and our conversations have recently escalated to how it will be when the time comes.

We are about 10 years apart in age. I’m 21 and he is 31, but that isn’t an issue for me because I have always been mature and dated older guys, although he is the oldest man I’ve ever even talked to. My big issue is that he has 3 kids from a 14 year relationship with his ex. I love that he is a good father and is always with his kids but I’m not quite sure if I am ready for that type of baggage (the oldest is 12). I really like him so I know once sex gets involved the relationship will move to the next level but I don’t want to get into something I can’t handle and end up getting hurt or hurting him. I am not gonna lie my biggest insecurity is with the ex-girlfriend. They have a long history (friends first) and 14 years together, not to mention the 3 kids so I know they will always have to deal with each other to co-parent.

He says that is in the past and they don’t even speak much but I find that a bit hard to believe. At this point I feel like I’m being blinded by the illusion of what it I want it to be and not really seeing it for what it is, but I also don’t want him to have to feel the effects of my previous heartbreaks and bad situations by never trusting or believing what he is saying. Also, if I do decide to move forward how long should I really wait before sleeping with him being that we have already connected with each other?  Please let me know where I should go from here. – Ms. Confused

Dear Ms. Confused,

Take your time. Take your time. Take your time. That man has been watching you and sizing you up every time you “ran into one another” in the neighborhood. Let’s get one thing clear: You were not casual friends. You didn’t socialize with him, hang out with him, been to one another’s homes, or even chilled a few times. Hell, you didn’t even have his number, nor were you friends on FB. Therefore, you were not casual friends. If anything, he’s been counting the days, hours, and minutes of when he was going to make his move, and he finally did.

I want to know what are you in a rush and hurry for? Keep getting to know one another. Keep the conversation open. And, eventually you will go out, but don’t put the cart before the horse.

Chile, some of you women when you meet a man you will start planning the wedding, the household, how many kids you’re going to have, what they will look like, and where you’re going to live, yet, you haven’t even slept with the man yet. You’re looking 5, 10, and 20 years ahead into a relationship that might not even materialize. That is the difference between men and women “dating” and “getting to know one another.” Women are thinking of the man of their dreams, while a man is thinking “Can I hit it?” And, “Is the p***y good?”

When a man is pursuing a woman he is not concerned and thinking if she is wifey material. He is not looking far into the future and wondering if she will be a great mom to his kids. He is not caught up in wondering what type of woman she will be when they grow old together, and can he take her home to meet his family. NOOOOOO! Men are not thinking that. Only women think about those things. You’re so caught up in the relationship of the future that you miss the tell-tale signs warning you, “HE IS NOT THE MAN FOR YOU.” Or, “TAKE IT SLOW AND GET TO KNOW HIM.” And, “STOP TRYING TO MARRY HIM AND YOU DON’T EVEN KNOW HIM. IT’S ONLY BEEN TWO WEEKS.”

If your instincts are telling you to wait, then wait. If they are telling you to take your time and get to know him, then take your time and get to know him. If your gut is telling you that you don’t want a man with baby momma drama, and he’s been with his children’s mother for 14 years, and you don’t want to deal with that baggage, then listen to your gut. LISTEN!!!

My question is why didn’t he marry her since they were together for 14 years? That is the tee-hee-hee-hee-hee! They were in a relationship for 14 years, why weren’t they married? Something is not right. That should always be at the forefront of your mind, and, hell, you should ask him. Of course he is going to have a very good reason and excuse of why they didn’t get married, but I’d be giving him the big side-eye!

And, though he may be a good father to his children, how can he walk away from a 14 year relationship and say, “We don’t really speak.” Uhm, no ma’am. They have 3 kids together. Girl, you be the fool if you want to, but they speak all the time. If he’s a good father and active in their life, I’m sure the mother of his children is calling him, and having him active in their children’s lives.

And, 14 years is a long time to get over someone and move on and decide to get into another relationship. Believe me when I tell you this, he is simply looking to sow his oats and get laid. He is making up for those 14 years of when he was in a relationship with one woman. And, that’s if he was faithful. (Watch him!) But, trust and believe, it may sound commendable he was in a relationship for 14 years, which can make him seem committed, but he is a freelancer at 31 years of age. Those two don’t add up. He’s committed to his relationship, but not his career? I’m curious to know what he does as a freelancer, and how long has he been freelancing. Again, these are questions you need to ask.

So, my suggestion is to keep it casual. Do not spread your legs for him. No ma’am. There are some unanswered questions, and lingering doubts, therefore, do not open yourself to him until those things have been resolved honestly and truthfully. Therefore, maintain the conversation, and continue to get to know more about him. There are some unanswered, and unresolved things he is not telling you. Your gut and instincts are accurate, so proceed with caution. And, if you decide to become intimate with him, and I hope you don’t, but please use a condom. It may be a foreign concept to him considering he was in a 14 year relationship with a woman, and I’m sure they did not use condoms. Besides, you do not need to be baby momma number 2. You’re too young and have too much going for yourself. So, enjoy your young years, have fun, and be glad that your instincts are kicking in and giving you some red signs. You’re too young to be dealing with baby momma drama and in particular that his oldest child is 12 years old. Hell, you’re barely twice the child’s age. SMDH! Girl, keep that man at a distance and pay close attention to his actions and words. They will tell you everything. – Terrance Dean

Hey Bossip Fam, what do you think? Share your opinions and thoughts below!

Also, e-mail all your questions Terrance Dean: loveandrelationships@bossip.com

Follow Terrance Dean on Twitter: @terrancedean

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author terrance dean
Make sure to order my books Mogul: A Novel (Atria Books – June 2011; $15), 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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