How will I know when I'm ready for dating?

When you figure it out can you let me know? I seem to fall into many of the same traps as you.

But to get back to you, this guy seems like a potentially good guy. I think you’re on the right track with the go slow and see how it feels but why pass up what may be a good thing?

Can I make a suggestion?

At this point – don’t overanalyze. Just go with the flow. If you analyze every word and every action, then you will drive yourself nuts and drive the guy away with your angst.

Let it flow.

Can I start by saying well done. I hope you are aware of the huge steps you’ve already taken in making such changes in your life.

I think that you are so much more self-aware than you were and being so cautious about jumping in with both feet suggests you are ready to put your toes in the dating pool again. Do as you’ve said and take things very slowly. I also think, when the time is right, you should tell any prospective partner about your history. Not in vast detail, but to alert them to your wariness. So they realise it isn’t necessarily what they’re doing, but that your fear or reticence relates to what has happened in the past.

Keep in mind what you feel is important in a relationship. Allow time for you to discover if a person is right for you before you invest wholeheartedly.

I think you are ready. A couple of years single is a good start to knowing you can be single and fine.

My advice is this time when you see a red flag, heed the warning. Get out.

Make your list of what you want in an SO. You have probably seen me suggest that to jellies on other Q’s. Honest, supportive, open book, responsible, and then you add a few more like, interesting, funny, likes to travel, likes reading, likes sports, whatever is important to you. Don’t just get into a relationship, because a guy asks you out. Be picky. It’s so easy for dating to turn into a relationship, whether the guy is the right one or not.

Where did you meet this guy? How old is he? Why is he single?

He sounds like a great guy, and I’d hate to see you lose him if he’s “the one”, but I really think it would be best if you date around a little at this point. Try to get yourself comfortable being around men, rather than “a man”.

7 years of crappy relationships and 2 years alone. I’d like to see you kick up your heels a bit before you settle into another relationship. Give yourself time and space to work on your ‘several large steps for 2016’ while dating around, having some fun, and accustoming yourself to different kinds of men.

Congratulations on taking a good, solid first step. The fact that you are asking means you are ready. Some people muddle through life in ignorance and never ask that question. You are way ahead.

So? Does he Geocache?

How long have you been in AA? Don’t they say to wait a year before starting or ending a relationship?

You have done the necessary work on yourself. You are ready to date, but perhaps you are not ready for an intense or exclusive relationship.

Your instinct to take it slowly sounds really good. You know what signs to watch out for.

Have some fun. You deserve it!

I still think you’re amazing and ready to date whenever you feel like dating.

If we were good friends, I would respectfully ask one thing…

What do you want out of dating? It doesn’t have to stay the same, but it makes it a lot easier to figure out when you’ve found a match if you actually have something in mind. Not necessarily about the person, but what you want from a relationship right then. Maybe it’s companionship, maybe it’s a partner in crime, maybe it’s just fun times, maybe it’s someone who makes you feel safe, or is your equal, or challenges you. It could just be an exciting weekend once a month. Part of the blind spot you’re describing is that you are kind enough to see the possibilities and good in people rather than their shortcomings at their worst. I’m guessing you don’t want to lose that about yourself, so instead of tempering it with protections or fear, maybe define what you’re looking for more clearly. It easier to kindly say someone isn’t what you’re looking for if you know what it is you want. The kindness may be more important to you than to them.

You’re reflective and honest. You’re a wiser version of you, with hard-earned knowledge, than you’ve ever been. Trust yourself, even if past results aren’t what you wanted.

^^ Can you write that to me, too? That was such lovely advice.