Weirded Out: He Objects to Friend Dating Ex

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Hey Whit:

I hope you can help me on this one.  Last week I was hanging out with friends, and I started talking to a girl, Haley, who used to date a friend of mine (he wasn’t there at the time), a good friend named Tyler. Haley is friends with guys who I know and she sometimes socializes with them, so talking to her was pretty normal, at least not unusual.

I didn’t know her very well when she was going out with my friend, but I thought that she was good-looking, and she seemed like a fun girl. Anyway, after talking to her for a little while, I felt that we had sort of a connection, and I wanted to go out with her on a date.

Just to make sure, I talked to my friend who used to date her, and he was pretty weird about it.  I was really kind of shocked that he couldn’t figure out why I would want to date her since she was “somebody who was the ex-girlfriend of a friend of yours—a good friend.” Why would he even care? Am I missing something here?

Missing Something

Dear Missing:

“Why would he even care?” My reaction exactly. So let’s consider what you might be missing here and why he would care.

Maybe Tyler treated her in a way that would embarrass him if you knew about it. Maybe Haley treated him in a way that would embarrass him if you knew about it.  Maybe something happened between them that Tyler doesn’t want you to find out.  You can use your imagination, but let me give it a jump-start.

Depending how long they were together, Tyler could have become bored with her; perhaps he reached the point at which Haley felt under-loved or under-appreciated. If they had dated for a long enough time that he started taking her for granted, Tyler could have become cold and unfeeling and checked out.  If he thinks that such behavior might be unflattering to him, Tyler might not want you to know about it.

Possibly they weren’t right for each other from the beginning, as far as Tyler was concerned, so that he just stopped calling her.  He might be the kind of guy who lets a mismatch go on until he decides that he’s had enough and then breaks off the relationship. Or possibly he found someone else who looked better to him. In short, he didn’t care about Haley anymore. In this case, Tyler is hoping that Haley doesn’t talk to you about how he was another example of “boys behaving badly.”

On the other hand, perhaps she didn’t care about him anymore. For whatever reason, Haley decided that this guy wasn’t worth her time and emotion and cut him loose. If that’s the case, then Tyler wouldn’t want you to know that he was dumped. He could be acting weird because he’s afraid that you’ll find out that a girl didn’t want him, especially if he’s a guy who likes to call the shots, or thinks he is.

You have to ask yourself whether Tyler is the type of person who would be honest with you if you asked him to tell you about what happened between the two of them. Maybe you could tell him that you are puzzled by his reaction and wondered if he could tell you what’s bothering him about your seeing Haley. If he can and does, then you will have a better idea of what his thoughts and feelings are.

In the final analysis, however, what you do or do not know, much less understand, about how your friend feels and thinks is immaterial.  By the same token, all he needs to hear from you (if you think that it is relevant) is that you have been getting to know a girl that he used to date, if you want to say even that much. But you are under no obligation to “clear” your relationship with Haley, whatever it is, with Tyler. Remember, she is a person not a possession and one over which your friend has no present or prior claim.

Got questions about life? Love? Parenting? Work? Write to Whit’s End, an advice column by local husband, father, teacher, coach, former executive and former Marine Corps officer Al Whitaker.  Send your questions to [email protected]

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  1. Some guys have a funny thing about girls they have dated in the past, like that even after they themselves don’t want the girl anymore, the girl somehow remains theirs. Kind of like dogs marking their territory. Sometimes it works in reverse, so that guys who meet a girl who has dated other guys they know won’t even think about going out with the girl, as if she has been spoiled by being with the other guy. It’s all pretty messed up, if you ask me.

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