I'm 24, and never been on a date. Whenever I meet women I always assume they're either married, already have a boyfriend/girlfriend or are just not interested in me. 

I'm not exactly an outgoing guy; I cherish my privacy, love sports, going to the movies, talking about film. I'm aspiring to be a professional filmmaker. I love museums, walking through the beautiful parks and sights that Chicago offers.

When I ask my now ex-friends for dating advice, they all say, "there's someone for everybody." But I feel there isn't a single person out there for me.

Growing up, I was bullied and made fun of by girls and I always thought every woman was like that.

Is there any hope or should I start investing in hookers?

- Fed Up With Women

You have many interests that many women would find appealing, but it's you who has to become open to meeting women and not pre-judging them from your past experiences. 

You're understandably shy and scared, but have wrongly decided to negate your possibilities of meeting someone. Instead, you need to bolster your confidence in your own self-worth. Start with your interests – join a film club, a museum interest group, participate in Chicago's popular walking tours, and/or a sports team.

Meet women as friends, without scanning each face for The One. Let your new female pals know you're open to set-ups with their women friends. And, please, don't rely on hookers to improve your relationships with women - they're sex workers trying to make a living, they're not personal therapists.

After Dad passed away last year, Mom moved back to her hometown overseas. I was left in charge of selling her home, while I live in another city five hours away. I spent weekends travelling to and from the house to make general repairs. My friends have been unhappy that I had little time to hang out. 

With the house sold, I have to find movers and a storage unit. Without any family nearby, I feel emotionally exhausted, like I’ve been running a marathon ever since Dad died. I’m angry that my friends are upset.

Recently, my siblings overseas said they need help covering Mom’s medical and housing costs. I feel burdened and unable to just be 24. What can I do to make things better and stop feeling awful and burdened?

- Depleted

You’ve been thrust into a position your friends will one day have, too – it comes with loss and sorrow, and only those who’ve experienced it can truly understand. You’ve handled your responsibilities admirably. 

It’s not your siblings fault that you’re the one available for those tasks; but then, they need to cover more of the tasks back home, and expenses need to be shared as equally as possible.

Grief is exhausting, but these chores are generally a healthy part of the process of coming to terms with life’s major changes, and being part of a family fabric during those times. Chill, when you can; forgive your friends for being young and complacent.

Plan for time together when most of the work is done… better to be with people than to sink into a letdown period that can be lonely and depressing. You’re still 24, with a full life ahead, knowing that you’re someone who does the right thing when needed.

Is it stupid to stop dating someone you like, and who makes you laugh, just because he dresses un-cool?

- Wondering

Yes.

I met a married man whose wife is in his home country; we became a couple for a month. He ended it, and then later asked me to come back. I refused. I think it’ll be better if we part ways. 

I haven’t seen him for four months, and then recently saw him with another woman. It hurts, but I know I was right.

I just don’t know how to forget him because I still check his Yahoo and Facebook accounts. I want to get over him.

- Confused

Look at reality instead of his personal networks – you were his Comfort Woman, nothing more. He’ll have others, until Wifey comes, when he may or may not continue to cheat. Feel lucky, instead of hurt. 

Your second instinct (not your first) was to protect yourself from far worse pain if you’d carried on for years, and deprived yourself of a real relationship with someone who’s available.