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Dear Bossip,

I am extremely confused about what’s going on with this guy that I like.

Here’s what happened. We both live in 2 different countries, 2 hours away by flight. To start out, we met thru mutual friends, and I later found out that he was attracted to me. I’ve just come out of my first serious relationship that lasted 6 years and had no clue of the whole dating world. But, I somehow gave him the go-ahead thru our mutual friend, and he took my number and started texting me when he went back home.

Things kicked off pretty soon. We’d speak every single day, from morning to just before bedtime. A month later, he came back to town for 3 days, without telling me. I never used to ask him when he was next coming into town to begin with. But, it was apparently a surprise. It was on this trip that he officially asked me out on a date. We went out for dinner, movies, and a concert that entire weekend and it was great. The weekend ended with our first kiss. And he was back on the plane again.

Our contact stayed the same, being in touch every single day, but I’d never ask him when his next trip would be, etc. I didn’t want to come across as pushy or clingy, etc. At the end of that month again, he texts me one night asking if I was able to take a day off work. If I was, he’d fly in the next morning. I was honestly flattered, never had a guy fly all the way to another country just to spend a day with me. I agreed and he was in town the next morning. He didn’t try to kiss me which I found interesting. He checked into his hotel room and asked me to come upstairs while he changed. I agreed. But funny enough, he made no move on me whatsoever in the hotel-room. I found him to be a real gentleman then. We spent the entire day together, alone at first, and with friends later on. The night ended with me dropping him off at his hotel, which is when he finally kissed me goodbye. The kiss got a bit more intense, and he then invited me upstairs. I hesitated, my mind was saying NO, but yes somehow came out.

Long story-short, the night went well and on checkout the next morning, he kept talking about how he didn’t want to leave and wished we spent more time together. Contact was still strong after he left for about a week or so, then that’s when things started dying down. We’d go a day or 2 without talking to each other. I didn’t start any convos with him though. I was always under the impression that the guy should start the convos.

Anyhow, the dying conversations carried out into the end of the month once again with a text from him on a Friday night saying, “Hey, I’m on a flight, I’ll be in town in 2 hours.” He called soon as he landed and asked what I was up to. I didn’t want to come off as desperate and willing to ditch my plans and I very coolly said I was going out with some friends, and he was welcome to join us if he’d like. I ignored him most of the night I have to admit. I would make small talk, but I mostly kept myself busy with other people. He luckily bumped into a group of his friends he hung out with most of the night too. The night ends with a goodbye hug.

The next day he text me a good morning and asked how I was doing. I cheerfully replied I was doing great. I was hoping that he’d ask to meet, but it never happened, so I made my own plans that night. Coincidentally I bumped into him at the same lounge I was at that night. We then brought our friends together and hung out for the rest of the night. He told me he was leaving town the next day and I wished him a safe flight. He didn’t call to say goodbye or anything the next day. And the dying conversations still go on. We now go a week or 2 without any contact.

My question…What the hell is going on?? I have to admit I really like this guy. I know I should have waited longer before sleeping with him. Did that sabotage the entire thing? I’m so lost. – Cross Country Fling

Dear Ms. Cross Country Fling,

Well, your Mr. Romeo is not really your Mr. Romeo. I gather that he is a man on the move, and a free-spirited guy who travels from destination-to-destination hooking up with attractive women and having these wild sexy fun and entertaining meet-ups. And, you just happen to get caught up as his newest fling.

The reason the communication was constant and consistent in the beginning was because he was selling you on the dream. He got you interested, intrigued, and curious. He made you feel comfortable, so the phone calls were consistent. He had to build trust with you. And, once he gathered the trust, he flew into town, called you up, and BOOM! You were available because you wanted to spend some time with him. He made sure you had a good time, made you think he was a gentleman, and he treated you special, and once your guard was down he invited you upstairs to his hotel room to seal the deal. Now, he’s got you! You’re hooked, and you’ve just become his newest jump-off without knowing you’re a jump-off.

Honey, this man never lets you know when he’s coming to town, and when he does he expects you to be available. That is a jump-off. Think about it: The man hits you up whimsically telling you that he is coming to town. There is no advance notice, or any indication that he will be visiting within a few weeks, or days. He just appears or shows up and calls you to see if you’re available. And, if you are, then it’s on and popping. You’re his good time girl, and it’s all about having fun and great sex. Besides, you did sleep with him after his second trip of visiting you. So, he figured that is what you wanted as well because neither of you discussed the terms of the relationship, or what you both wanted.

You notice that when you made yourself unavailable he still continued to party and have a good time with his friends. He was unbothered and went out on the town having a good time. And, lo and behold, you bump into one another and he’s still having a good time. If he was all about you and wanted to spend time with you then he would have made a much larger effort of speaking with you that night, and attempting to make plans with you while he was in town. But he didn’t. So, I surmise that he’s not looking for a woman, a girlfriend, or to make you his special lady. You’re just someone to hook up with and have fun with while he is in town. Because when he leaves to go back home he is going home to someone else. Trust!

Uhm, ma’am, I don’t know what he told you, or what he led you to believe, but, err uhm, if this man is attractive, successful, traveling frequently from country to country, and always out on the town having a good time, then please believe that he has other women lined up who party with him, and he has a woman at home.

For heavens sake, the man lives in another country! HELLO! He can tell you anything. He can have a girlfriend, wife, or a plethora of women at home. But, when he comes to your country it’s all fair game. He’s off the leash and is looking to have a good time with a woman he can visit on the regular without any commitment. That is why he never lets you know when he is coming to town. If he can’t commit to a date with you in advance, and he just pops up, then it should send red flags that this man likes being a mystery and lives his life spontaneously. Which also should tell you that he is hiding something.

I’m curious as to why you never felt the need to ask him when he was coming to town. But, more importantly, you should have set the boundaries of the relationship by informing him that he can’t just pop up and call you unexpectedly and think you’ll be available. He has to treat you like a lady, and not like a jump-off. Only jump-offs are ready at a moments notice when their man suddenly appears in town. Only jump-offs have to schedule their lives around a man who keeps secrets and makes no plans for their dates. Jump-offs live their lives waiting on the man to call, hoping he will be available, and when he calls they are ready, willing, and able to “Jump-off.”

So, it’s a lesson learned. You can either call him and ask him how he really feels for you, and if he is seeking something serious. Which I doubt he is. Or, you can ask him if he is just looking for someone to spend time with while he is in town, and have a good time (Friends with benefits). Which seems more like him and why he doesn’t feel the need to tell you when he is coming to town.

Regardless, if you decide to continue seeing this man, and you get the answers to your questions then you have to decide if he is worth it. If you want to just have a good time with him while he is in town, then set some boundaries. Let him know that he can’t just call you when he’s on his way, or he is already in town. He needs to give you at least a week’s notice because you may have plans, and you’re not going to interrupt your life for him if he is not going to respect your plans, and what you have going on. So, let him know that you’re a lady, a grown woman, and you’re not going to play his game. The rules have changed. If he wants to play, then it’s on your terms.

Also, I do strongly urge that you ask him if he has other women, or a woman, girlfriend, or wife at home. He needs to be open and honest with you because you don’t want to get caught up with some other woman’s man. Now, that is something I don’t condone. Hopefully he’ll be honest and tell you the truth. If he is seeing other women, or has a girlfriend, or if he’s married, then leave him alone! Cut him off and have nothing to do with him. You don’t deserve to be second, or to play mistress. It’s not cute. So, call him and get the answers to your questions. You deserve more. – Terrance Dean

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