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? Do you have any experience involving 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.

You should really ask her, and here’s why: she’s dating someone, so it’s not like this she’s just start dating your brother. 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), it could cause some unintended side effects on your friendship. How would you feel if a good friend started complaining about what a jerk your brother is?

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.

l l l

I am 19, soon to be 20. I am in love with this guy who is 25. We have known each other for a while and talked once when we got into our church group gathering. The only problem is we are both shy. I have never dated before, and have no idea how to approach him. What is the best way that I can tell him the way I feel? I have been told to write a letter or go up to him and tell him, that I love him. I know it sounds easy, but I am nervous. How can I show him or tell him that I like him?

-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?

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 still have no relationship. Nothing to lose, a lot to gain.

l l l

I’m dating a 25-year-old girl and we have been dating for 6 months now. I’m 19. We do have similar interests, and we are kind of similar 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 Master’s, and I’m just getting to my Associate’s now, which is another hamper in it. We both like each other; I am just 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, however, come out of sheer boredom with the relationship.

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.

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?”

Good luck, and thanks for asking.

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