A Word of Advice... on dating

By Joshua O'Connell
Posted Monday, September 1, 2003

I have become good friends with someone since December, and when we became friends I told her I was interested in her brother. She is 21, I am 20, he is 18. She is attracted to my brother who is 22 but she is dating someone, and we have joked about dating brothers and she said she wouldn't want to put me in that awkward position. So is she also saying I couldn't date her brother without saying the words? Does anyone have any experience with dating friends' siblings? I have fallen for him, but with her latest comment I am afraid there's no hope.

--Can I date him?

Cue the Family Feud-type buzzer: you're asking the wrong person. (Sadly, a lot of my columns have started out this way lately. Wrong question, wrong person, etc. It's not by choice, believe me... it gives me less work if you don't come to me.)

You should really ask her, and here's why: she's dating someone, so it's not like this situation would happen initially. Ask her how she'd feel if you asked out her brother. After all, he might not be interested in you, so it might not happen.

But even if it does, keep in mind that many relatives aren't always happy that someone's dating their brother, sister, aunt, first cousin twice removed, etc. If you think there might be something, go for it, but if you feel you need her blessing, ask for it.

Remember, though, that if bad things happen between you and her brother (assuming the dating begins, of course), that could cause some unintended side effects on your friendship. How would you feel if your good friend started complaining about what a jerk your brother is? Wouldn't be fun, right? So remember that this will affect the friendship if you don't play it careful (again, assuming you do end up dating him). And also, remember that the friendship was first, and there are other guys out there, so even if you don't get the chance, or if she says she'd be too uncomfortable, it's really not the end of the world.

--Some help, yes?

Your problem, SHY, is definitely one I've seen before. You do need to tackle this, and I suggest approaching him, not a letter.

You see, if you send a letter, you're hiding behind the pen and it won't allow you to get over the initial shyness. You've said you've talked to him - you already have spoken to him. He didn't bite you, right?

Now, buzzer time: one thing you should not do is tell him that you love him (you say like at the end, but love came first in your letter). Yes, you may be in like with him, but love? How?

The age difference will likely pose an issue here. He may turn you down. But I also believe that when you ask someone out, you've entered the situation with nothing - you have no relationship. If he turns you down, you have no relationship. Nothing to lose, a lot to gain. Just make it clear that you'd still like a friendship if that doesn't work out - having him in your life in some has to be better than nothing at all, right?

Of course, since WinAmp just selected "Don't Let Me be the Last to Know" by Britney Spears out of a song list that's over 750 songs long, I don't know if you should take my advice. She's making me all emotional. *sob*

--Good responses, please

"If you change your mind, let me know." Or, if you want to prod her a bit, and risk pushing her away further, "Why are you afraid you'll hurt me?" If she's honest with you, and things come out, you might understand a bit more. And that might build a bit of trust that could help. But it could also just be annoying. So tread carefully.

I'm dating a 25-year-old girl and we have been dating for 6 months now. I'm 19. We do have similiar interests, and we are kind of similiar as far as wanting attention from others.

Well, we have been breaking up, becoming friends, then dating again.

She has problems getting over my age, and we have problems communicating, which is my fault because when we do something I have problems coming up with something interesting.

Really, I just kind of want advice and such with dating a girl that is older, she has her masters, and I'm just getting to my AA now, which is another hamper in it. We both like each other; it is I am having problems communicating with her.

--'Tis aggravation. Lend knowledge

Let me "communicate" a few things here. The buzzer's getting a workout today.

First, having problems communicating cannot possibly come out of bad choices for dates. Relationship problems can come out of sheer boredom with the relationship, and if you two don't have favorite haunts, or interests in doing new things together, that can hurt things a lot.

Second, TALK, blaming yourself for a relationship's problems is no way to solve this either, at least in your situation. There's an age gap causing issues between how you two communicate with each other. If your "communication problems" are mainly because she's got a master's degree and, supposedly, a bigger vocabulary as a result, that's not the problem. The problem really is working around the age difference, something you two haven't done.

Find activities that you both enjoy and do them. You say you have similar interests - explore them further. If she's having problems getting over your age, that's something she has to work on. Ditto if she's having problems with the choices about where you want to go. The age difference just might be too much for her to get over. That's not your fault if that's the case. But if you two are going to work on the relationship, the real question to ask here is "What can we do to get over these hurdles?" Furthermore, you need to talk to each other and ask each other that exact question. Good luck, and thanks for asking.

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