Ask Dave-Am I ready to date again?

Post-breakup, how do you tell if you’re truly ready to get out and flirt online? Here’s your answer.

By Dave Singleton

ear Dave,
About six weeks ago, I broke up with my boyfriend of two years. For the last six months of our relationship, our physical life was dead. We very rarely had sex, maybe about once a month, if that often. After several months and numerous arguments, we finally called it quits. Now I am exploring
This sounds like a budding romance to me.
online personals and have met this great guy. He is very nice and treats me well. We both stated upfront that this would be just a friendship. He was in a few long-term relationships, lasting several years each, until he just became single about six months ago.

I truly believe that I’m starting to have romantic feelings for him. I think about him all the time. And based on how he acts towards me, I think he is interested, too. We talk on the phone every day at least four or five times, and though we have not had any physical contact, I think it’s just a matter of time.

So my question is: Do you think I am acting out of haste due to a recent breakup, or can this be the real deal? This is the first time I’ve actually looked forward to spending time with someone on an intimate level. I would like to possibly pursue something more than friends with him, but I don't want to turn a blind eye to risks, either. Can you give some advice on how to handle this?

Dear William,
You talk on the phone four or five times a day? You think about him all the time? You say that this is the first time that you’ve ever looked forward to being intimate with someone?

This sounds like a budding romance to me. Of course, you can meet a new friend and get excited, too. But my guess is that there’s more to this story, especially if you sense some reciprocation from him.

It sounds like a “Proceed With Caution” sign was flashing in the background when you two met. Given your circumstances, I can understand your wariness. But I can’t think of a reason why you shouldn’t pursue a romance with this man if your feelings are leading you in that direction. Of course, before you can do that, you have to deal with your concerns.

First, is this a risky situation? Yes, dating itself is risky. You never know what will happen or if Mr. Maybe could morph into Mr. Right. But keep risk in perspective. I understand that you don’t want to harm your budding friendship. But I don’t see this as the major hurdle it might be if you had a long history together. Since you’ve only known this man for several weeks, you aren’t risking years of friendship or endangering
It’s also important to respect his feelings about dating you.
a trusted platonic bond. Whether it’s a friendship or a budding romance, it’s still a new relationship. It’s not as hard to change your status from friends to dates now as it might be later.

Second, is it too soon for you to pursue a new relationship? No. I don’t think you are acting out of haste. On the contrary, you aren’t acting at all yet. You haven’t made a move or shared your true feelings. This is entirely understandable, especially since your breakup is fresh. The thing to keep in mind is that romantic timing varies by individual; what’s right for you might not be right for someone else. For whatever reasons (probably fear and post-breakup confusion), you weren’t ready for romance when you met him. But maybe your burgeoning feelings are signaling you to try again.

Third, do you tell your friend how you feel? I would, but only after taking some time to consider your circumstances and motivation. Double-checking your feelings before speaking to him is a good idea.

Is this genuine interest in him, or are you feeling the pangs of post breakup loneliness? What were some of the issues that affected your last relationship, and what have you learned from them? From as objective a position as you can take, is he the kind of boyfriend you’d want?

When you tell him how you feel:
  • Acknowledge the friendship. Let him know that you hesitated to tell him the truth and risk losing this budding friendship. Your honesty reflects your consideration for the friendship.
  • Be yourself. If it’s a solid romantic match, it will feel right. If you feel comfortable around him now, hopefully that ease will translate well if you start dating.
  • Respect his decision. While it’s good to be honest, it’s also important to respect his feelings about dating you. If it turns out he’s not interested in dating you, accept his decision and move on as best you can. Keep yourself busy with friends and, if you feel up for it, click on a few profiles and see who else sparks your interest in the online personals world.
Bottom line: After a few weeks of this new friendship, you have little to lose and a lot to gain by making a move. Even though you’ve both experienced relatively recent breakups, readiness for a new relationship is an extremely individual decision. The best advice is to go slow. If dating this new man works out, proceed at a pace that feels comfortable for both of you. Post-breakup, you might be ready to start testing the dating waters again. But that doesn’t mean you’re ready to dive into the deep end so soon.

Dave Singleton, an award-winning writer and columnist for since 2003, is the author of two books on dating and relationships. Send your dating questions and comments to him at
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