I’m 20, female, and have a male roommate. His best friend used to come over a lot. Three months ago his friend texted me and invited me out with him that evening.

We ended up sleeping together – unusual for me, but I was very drunk. We kept in small-talk contact after, about once a week.

One month later I decided, well, I have needs, so I sent a suggestive text. He got the signal immediately; we hung out the next day and had sex.

He now contacts me every three or four days to have sex.

Soon after, he was at a club I went to, so we started dancing and he eventually repeated, "I like you." I brushed it off because he was high and I figured it was because of that. We went home together.

When I asked him about it the next day, he avoided the question, saying sarcastically "Oh no I tooootally don't like you, I haaaate you.”

I never gave him ANY inclination of wanting to date or have anything more. We continued hooking up every three or four days, but our conversations got VERY intimate and deep, even how he’s contemplated suicide in the past. Things that I didn't think "sex buddies" usually talk about. He always sleeps over after sex and we cuddle most of the night.

Recently he told me all about his aspirations, dreams, and goals, and asked me numerous personal questions and wanted to know about my goals. I can't understand why.

He even asked if I’d slept with any of the guys he knows are my friends. Why does he care?

What should I be doing? I've started to like him, and I hate myself for it, but there's nothing I can do about it.

Getting Involved?

You seem unnaturally surprised that a sexual connection can lead to emotional attachment, as if hooking up comes with a contract you both signed to never care about each other.

You’ve taken the label “Friends with Benefits” too seriously, and not recognized the normal feelings between two people who’ve grown to enjoy getting to know each other.

You now need to also apply understanding and compassion to this guy. He’s revealed some deep events in his life, with even deeper repercussions that caused him to feel suicidal.

Do not mess him up. Of course he likes you - he said so. Stop acting like a kid who’s naive. If you’re old enough for regular sex and drunken mistakes, be mature enough to know when something more serious is developing.

If you’re not going to let it grow, tell him so. It’d be far crueler to cut and run.

We have a vacation home in Florida and don't want any adult children to visit. How do we tell them they are not welcome?

Loners

You’re hoping I have some magic words that can make your request NOT sound distanced, disinterested, or even be seen as selfish by adults who’d love an inexpensive break in their parents’ home under sunny skies.

Sorry, but you’ll have to be honest, and risk alienating them. But you already knew that.

IF you’re not against seeing them, just don’t want them messing up your pristine home (either with their presence or their family dynamics) you could scout the area for affordable places they could rent for short periods.

That way, you could all have a family get-together and they’d have a winter break. Or not.

I'm 16 and have been best friends with a boy for four years. We care about each other and confide in one another about everything. I’ve grown feelings for him and have admitted my feelings to him.

At first he said he wasn't sure of his feelings for me, but later told me he doesn't like me back.

How can I get him to see me in the same light I see him?

Uneven Match

Be yourself, it’s the only way he should see you. Do NOT change your personality or copy anyone else, in hopes it’ll attract him more. He knows you well, as a close caring friend.

He was honest with you; accept it. Perhaps he feels “dating” would ruin the friendship…. it can. Perhaps he’d like someone with whom he’d see how far he could get physically. But he has more respect for you. A deep friendship means more than a crush.