I’ve been single for four years, have a grown child, and great relationship with my ex. I’m living my life and my independence.

I’ve met a man with whom I think I may see long-term potential. He's very caring, supportive, and fun. However, he's been single for only one month!!
He’s getting out of a ten-year relationship. They have children. He's told me he has no desire to reconcile.
He seems to allude to her having an affair.

Is this too much baggage for him to be moving toward something else? I’m happy to put my feelings in check and enjoy the friendship. But only so far.

Help!!

Get a grip and help yourself! Think what you’d say if your grown child suggested taking someone seriously who’s “just getting out” after ten years and with a child.

It’s too soon, and he’s too slick with his “no-reconcile,” and too fast to be coming on to you as a single, available man. The reality is, anything can happen.

Hold in check your feelings AND any plans, expectations, promises, sharing of your home, and any other suggestions including exclusivity, for at least six months.

I’m 14 and my brother’s 18. We’ve known this other boy since I was age six; our families have known each other for a few decades.

This boy and I were always insulting each other and being rude to one another when we didn't agree. He would call me fat and ugly, and make me cry (typical boys). So, for obvious reasons, we were like brother and sister.

When I was age eight and he was nine, we were playing a game that involved nerf guns and being on a team of two, against my brother and his friend.

He randomly asked me "do you want to see my penis?" I declined the offer. He kept pushing the question and I finally gave in.

He showed me, and I was disgusted!

Later, when I was 11, I developed a crush on him.

I messaged him using a social media website asking him if he liked me. He messaged me back saying, "not really. But kind of." He told me that he had a girlfriend.

I was embarrassed.

I haven't spoken to him since 2011. Recently, he randomly messaged me and asked if I was nervous for high school, how my parents were, and he gave me his phone number.

Now, my feelings for him have returned! Do you think he may like me back? It sounds silly, I know, but I need some feedback.

Young and Uncertain

It’s not silly to be young and have someone play with your feelings, which is what he’s doing.

Maybe he’s bored, or just broke up with his girlfriend. He knows you once reached out to him, and that you could have feelings for him.

So… stay cool. You can respond as an old friend, but don’t be too eager or too open.

At 14, you’re facing years of needing to choose wisely, and not be talked into random penis-viewings or anything else that your gut instinct says you’re not ready for, or don’t want at all.

Don’t get into constant messaging with him… it can distract from getting to know friends at hand better, and enjoying school activities, etc.

Instead, it can start you daydreaming and building up expectations beyond what he intends.

You’re ready to start developing confidence in your ability to judge when to get closer with a boy, and when to hold back until you’re sure he’s sincere.

I'm 24, female, well educated, very attractive, and professional. I'm also woefully single, never been in any relationship, but have dated. I was busy with school, work, and chasing a career.
I have a hard time trusting men, because my own father had wandering tendencies. It's difficult for me to open up and be vulnerable to rejection.

Also, I barely have time to date anymore, working 100+ hour weeks including weekends.

No Partner

You’re not woeful, just overly wary. Your father’s wandering doesn’t have to be your experience.

But you’ve walled off, with workaholic barriers and a suspicious mind. Use your smart, professional mind to assess men on their own merits, and open yourself to normal dating by being friendly and making some time.

If a guy’s not interested in having a relationship, that’s not rejection. It’s just part of the selection process you’re both entitled to exercise.