Dr Date

Dr. Date,

I went on a second date with a guy, and he ended up sleeping over, and we fooled around a lot. It was fun, but now I’m worried that we will only do that because he expects it every time now.

I actually like him and want to slow things down, almost as if that night hadn’t happened. How can I make sure we both want the same thing?

—Oops

Whoo,

Dr. Date,

I am writing you because I need your advice on what to do when you have a crush on your teacher. This teacher is actually a graduate student but is still a few years older than I am. This teacher does not wear a wedding ring; however, I don’t know if he is even single. But I can’t stop thinking about him! It may be all in my head, but I swear there is a connection there. Is it too inappropriate to make a move? If not, how do I go about it?

—All I Want For Christmas Is Him

Mariah,

Dear Dr. Date,

Do you think exes can be good friends when one of them is still in love with the other? My ex and I have been good friends since our breakup in the summer, but he has been treating me in a way that makes me think he still has feelings for me. However, when I asked, he told me that he only viewed me as a good friend. Should I cut all contact with him or should I remain friends with him? I want to move on, but I am afraid that if I unfriend him now, we could never be friends again.

—Torn Ex

Ex Ed,

Dr. Date,

Dr. Date,

This guy I just started dating keeps asking me for nudie pics. I’m all into Snapchat but not for that. I think he has this impression of me that I do that kind of thing right away for guys, which used to be true, so I see why he thinks that. But I actually like this one and don’t want to rush the sexy things. How can I nicely tell him he has the wrong idea about me without coming off too prude-y?

—Saved

Prudence,

Dear Dr. Date,

I dated a guy 80 miles from here for about a year, two years ago. There was a five-year age difference between us, and toward the end of things I caught him sneaking around using Grindr. 

I wanted to work things out, but he did not, and the relationship ended. He’s been dating someone new and closer to him for a year or so now — they even got cats together. Several months ago there was a brouhaha because my ex and I had sex — he told me he was single — but the new guy found out. Amazingly, they are still together.

Dr. Date,

I’ve got my eye on a cute barista working at Espresso Royale. We keep making eyes at each other whenever I go in to study. I’ve caught him looking my way from behind the counter and smiling a little extra whenever I go up to buy something. How do I make a move on this cute coffee maker or get him to initiate the same?

—Coffee Shop Girl

Espresso Royalty,

Dr. Date,

OK, so I have a problem that I need your help with. There’s this guy and his sister. I like the guy a lot, but I’m also attracted to his sister. I’m not a lesbian or anything. It’s just feels weird to me. The guy is one I can settle down with, but the sister is like that one college experience. What should I do?

—Family Confusion

Happy Daze,

Dr. Date,

What’s the best cure to get over a really heartbreaking breakup? I mean the bad kind. The madly in love one day and tragically crushed the next kind.

Not to mention for a few months the situation was severely complicated: We lived together beforehand, and our separation didn’t change that until a few months ago. We were civil. I didn’t spend much time there apart from sleeping on the couch (though she offered to sleep on the couch, I declined. Always the
gentleman …).

Dr. Date,

I’ve been assigned to do some group work with a guy that I’ve been eyeing all term. This would be a great opportunity if I weren’t so socially awkward. At this point, I’d be happy just coming across as intelligent and normal and making a new friend, as opposed to being wonderful, flirty and charming. Help, please? Also, would making cookies for the group be a good idea or too much?

—Study Buddy

Buddy Shy,

Awwwwwwww … kward.