Tag Archives: will he date me

College Freshman Dating A Highschool Senior? Not Likely!

Dear Rob,
I recently confessed my affection to a guy friend of mine and to my surprise, he felt the same.

We sat and talked, discussing if we wanted to become more than friends. He suggested that we go on a date, to see where we could take things. So we go out and things are going great. When people ask him if I was his girlfriend he tells them I am. But we get back to his car, we start to discuss our relationship in detail and he reveals to me that he is unsure about us because while I’ll be starting my senior year in high school, he’ll be starting college at a school an hour and a half away from me.

I started to become frustrated with him because he keeps telling me that he really likes me (even mentioning examples) but how he is somewhat swayed by “outside forces”.
He is a very smart guy and a very logical thinker. That’s why he’s had so much trouble deciding. He begins to tear up because he “doesn’t know what to do.”

We decide to leave and head for a park to walk. So while he’s driving, I tell him that I’m sorry… that I shouldn’t have put all that on him but it’s just I have such strong feelings for him and I’ve heard the “long-distance relationship insecurity” thing before.

We both start crying and he tells me that he’s sorry too and I admit to him about my past relationships and how they never seem to work out and he tells me that any guy that wouldn’t want to go out with you is crazy. So we get to the park and talk and have an amazing time. We come home, kiss, embrace and I tell him that I want to see him before he leaves. but since that day, I haven’t received any communication from him although I see that he checked my myspace page quite frequently after our date. I told him how I felt about the whole thing but I haven’t talked to him since. I’m trying to give him his space but it’s coming down to the wire. And I really care about him but I don’t know what to do. I feel emotionally exhausted about the whole thing. 🙁

Thanks for reading. Hope to hear from you soon. 🙂
Hopeless in Colorado

Hi Hopeless,
This guy doesn’t need his space. He needs his life. And what he fears most is that he’s going to be a college freshman dating a high school girl.
Trust me, it’s not going to work. There is distance and the school bias working against this. Your guy knows this although he also knows what he’ll be missing if he doesn’t date you now.

He’s already showing you his doubts and, with distance and a new life and the college world in front of him, your relationship won’t last if you let it get started. And he’s ignoring you so that he doesn’t have to say this to your face.

Remain his friend but know that your lives are about to take different directions. Do not get involved at this point. If he asks you why you’ve decided to remain friends tell him what I told you.

And next summer, should you both be single maybe you can really become more than friends. But not before. Too many changes are going to happen to him, and you, in the coming months.
Best wishes,

Get His Info And Watch For Opportunity

Dear Rob,
I am a 40 yr. old, divorced single mother. A few months ago I moved into a new apartment, and there is a guy that lives in the building that I am interested in getting to know, but I have no idea how to go about it… or even if I should! ( I don’t know if he has a girlfriend, although I have never seen anyone.)

I do know he is also divorced, and he has two children. I know this because my landlord’s daughter, who is a friend of my daughters’ has talked about him to me. ( I didn’t ask! ) Apparently he is good friends with my landlord, and also works with him. I have thought about asking the landlord, or his wife something like “So, what’s Jeff’s story? Does he have a girlfriend?” But at my age that just sounds a little teenage-ish.

I have never had a conversation with him, we have said hello, and he always waves and smiles, even when he passes me on the road! I have tried to “happen” to be outside when I know I may run into him, but that hasn’t worked! What, if anything, should I do?
“A little out-of-practice”

Hi A Little Out Of Practice,
It’s fair to ask around about Jeff’s ‘situation’ before you make any moves.
This is not teenage behavior unless you stoop to the “does he like me, I like him” round-robin routine that teens do.

And I say that if he’s single, unattached, the next time go beyond saying hello to him. Ask him about his car, where he gets it repaired, you’re having trouble with yours. Something like that.
Maybe you need a quick hand getting something off a high shelf in your apartment. Something funny like changing an out of reach light bulb. You know what I mean, right?
Open the lines of communication. Don’t be afraid of making the first contact moves to get a conversation going.

After two or three of these mini-conversations if he doesn’t ask you out for a coffee, you go ahead and do it. Say to him “I could use a break, would you like to go to XXX place for coffee in half an hour?”

No matter your age, asking people in the know about someone’s personal relationship status, and I mean only asking if they are single or not, is OK to do. Just don’t get snoopy or to inquisitive.

Having the courage to initiate contact with someone is hard. Losing out on what could be a great experience or relationship is a downright shame.
Best wishes,