Q)I am re-entering the dating world after eight years with my ex, Karen. We started drifting apart a year ago, and I thought we were experiencing the typical ups and downs of any long-term relationship. But it turns out she had her eye on someone else. To make a long story short, we broke up in June, and it’s been an awful summer. I didn’t feel like going out at all. I have gone through so many stages — shock, anger, sadness — and now I finally find myself wanting to date around and really experience lots of women. That’s one thing I never did and I feel like maybe I’ve jumped into relationships too quickly.

The idea of going on a date, however, just seems scary. I am used to doing the everyday things that Karen and I shared, like taking care of the dogs, making dinner and working on the house. I feel like I’ll be a complete disaster on a date. I worry that I’ll pick the wrong place or say the wrong thing. When I get nervous, I blather on like an idiot. Although I notice attractive women more these days, my fear is holding me back. What advice do you have for me?
-Getting Back in the Saddle

Dear Saddle,
Getting back in the saddle is never easy, especially after your horse throws you. Getting dumped so quickly by a long-term lover is as much of a shock as being hurled to the ground—and possibly as painful.

Instead of focusing on the scary “what ifs,” be more proactive. Think of dating as a muscle that needs to be exercised. If you asked my advice about starting a new workout regime after years of atrophy, I’d tell you to walk before you run. The same goes for dating. Take it slow.

That said, I think you are smart to date a number of women without focusing on your next relationship. From one serial monogamist to another, I assure you that the time you take to explore your options will help you learn more about yourself and what you want. It will also give you time to clear out the bad energy from your breakup and get in “dating shape.” Focus on yourself and have fun meeting new people for a while. When Ms. Right does come along, you’ll be better prepared emotionally.

Remember the old adage that you never get a second chance to make a first impression? It’s especially true on a date. Avoid disastrous first dates by following these guidelines for where not to go and what not to discuss.

Where not to go:
The place where everyone knows your name. Instead, pick a cool, out-of-the-way place to meet. Sometimes the gay community can be too small for our own good. Many of us tend to hang out in small, gay-friendly neighborhoods, which is great if you enjoy running into friends, but it can backfire on a first date. Don't go to your version of “Cheers" if you want to spend some uninterrupted date time.

Noisy, crowded restaurants or bars. Thanks to the growth of online dating, “quick-meet” coffee dates have become a popular way to meet. It’s smart to get acquainted in relative peace, someplace you feel comfortable, versus a place where you can’t hear yourself think.

Anywhere that reminds you of your ex. Places that you and Karen frequented together should be considered off-limits for now. It’s natural to associate certain places with certain people, so don’t risk meeting new women anywhere haunted by the memories of your former relationship.
What not to say:
Anything that mentions Karen. In fact, ax the word “ex” from your first-date conversations. This is especially important given your recent painful breakup. You are liable to express hurt, bitterness, and/or anger—none of which paint you in the best light. The term "ex" shouldn't even come up during the first few dates.

Enough about me, let’s talk more about me. While being nervous is understandable, you’re smart to worry about saying too much on a first date. If you sense the onset of nervous “motor mouth,” take a deep breath and stop yourself. Instead, try to keep the conversation balanced by asking questions about her interests and passions.

Too much about the future. If you are having a nice time, you might feel tempted to suggest future plans (i.e., “We both love to ski. Let’s go on a ski trip.”) In a word, don’t. Loneliness sometimes makes us want to skip the essential “getting to know each other” steps in order to experience the same kind of closeness we had with a previous partner. But you can’t force real intimacy. If you feel things start to speed up, slow them down.
Bottom line: To make the most of a first date, pick a comfortable place that’s familiar, but not overly so. Your surroundings are a big part of first impressions. When it comes to conversation, ask questions that show you’re interested (and to keep you from nervously talking too much