Samara O'Shea


Dear ​Samara,

I am dating this guy who has been texting me at the last minute to go out. Does that mean I am his last choice? Either way, how do I get him to be more proactive?

Waiting by the Phone


Dear Waiting by the Phone,

You nailed it. You are not a priority for him. I know it’s easy to chalk his behavior up to the way things are done these days. “Hey man, technology. Nobody makes plans more than, like, 12 minutes in advance.” But they do. I’m sure you give your friends and loved ones the courtesy of more than a few hours’ notice when you want to see them—just as this guy should be doing for you.

The first rule of any relationship (new or old) is: You can’t change the other person. So there is no way to “get him to be more proactive.” He either wants to put time and effort into this or he doesn’t. Disappointing but true. I say tell him that you need more notice (maybe even a whole day) before getting together and if he disappears, good riddance.



Caroline Wales

Dear Caroline,
I am 46 years old and divorced twice. Online dating depresses me because the men who are interested in me are my Grandpa’s age, and I am not sure how to get back in the swing of dating in a positive way.
Depressed from ​Online dating
Dear Single and Ready to Mingle,.

Dating can certainly be a trying adventure. Truthfully, I’ve never really liked dating. It takes so much time and energy and it can be an intense emotional roller coaster. Still, good for you for staying open and putting yourself out there. It’s so important that we keep doing this no matter what our hearts have weathered.

That said, with two big relationships behind you, if you haven’t already looked inside yourself to ask the question “what do I really want from this dating experience”, further “what kind of relationship or love am I really looking for”, then take a bit more time before you enter into this world. If you don’t enter it with a grounded sense of Self, and a healthy level of self-love and acceptance, then you may not be ready for what shows up. There isn’t a woman (or man) out there that I don’t advise to first invest in a full relationship with themselves before they look to someone else for love. If we don’t take this initial step then we are setting ourselves up for more heartache and entering into new relationships with old patterns, or at least old patterns that we have yet to shed light on.

I was once told that when ready to begin dating again, don’t write out a prescription for myself of what kind of man I must have. This is not to say that we don’t have standards. In fact, the more time you spend loving yourself, the higher your standards for potential partners and the more likely you are to attract what it is that you are truly seeking in a mate (or “right now” friend). Once you do put yourself out there, you choose how you want to do it. Just because online love is the new big thing and “everyone” is doing it, doesn’t mean it’s right for you. I personally wouldn’t choose the local dive bar, but I think you get what I mean. Try meeting people doing things you actually enjoy doing, lest you meet a man who truly believes that you love hiking too, and then you’re screwed because you cannot make a good or sexy impression drenched in sweat, tears, and bug bites. There are people everywhere looking to meet someone just like you. Unfortunately, as every older, annoyingly wise woman has ever said, he will show up when you aren’t looking. Translation: he will show up when you are enjoying the hell out of yourself, not even caring about how hot he is in a pair of cotton Dockers!

There really are men out there your age looking for women like you, but you will have to sift through a lot of undesirables to find him, online or no. But I think that can be a good thing; You get to practice saying “no” to what’s no good for you. You deserve to be picky, after all, you are a divine woman like the rest of us who have spent life times denying ourselves good things because we have forgotten about our divinity. Take your time. Take a deep breath and smile. Go on dates with the intention of making a new friend as opposed to a life partner. Love takes time to bloom. And don’t be afraid to find or open yourself to love from strange or unexpected places.

He’s out there. I’m sure of that. This entire affair is so much more about your personal process than anything else. He is just the icing on top of your cake, baby! So enjoy this. Don’t let yourself go to that unhappy place. There’s just no need for that!