The Complete Guide To Getting Your Ass Back Out There

Close your eyes and recall your very first “official date.” Was it back in junior high school or after college? Visualize the total experience, where did it take place? Were you excited to be with him/her or was it more of a chance to try “dating?” Were you comfortable being with him or was it awkward? Did you have dates that turned into relationships or were you more of a serial dater?

Other than accepting a boy’s I.D. bracelet in sixth grade, my first “official date” was in high school. The subsequent dates were more about the perks of dating versus boys that I enjoyed being with. These guys came with benefits such as; I’d have a date for the Homecoming Dance, or because his dad let him drive the bright green Cadillac. Senior year I started dating a guy named, Tommy who was actually fun to be with, but had an added bonus of being a college boy at Northwestern. It held a lot of value until I myself left for college. Being free to date in college, experimenting sexually, and falling in love changed the landscape of dating for me. Meeting my husband and getting married right out of college, put an end to my dating, or did it?

Fast-forward your mental slideshow 10-30 years. Call to mind your first date as a widow or divorcee with kids and an ex-husband.

What was that first date like for you? Did you get fixed up or did he ask you out after meeting you in a bar? Were you feeling the same awkwardness as you did back in high school? Was your confidence level the same or different dating this time around?

My lack of dating in my 20s and 30s had its pluses and minuses when it was time for me to get back out there. On one hand, I had plenty of self-confidence having never experienced rejection. On the other hand, I was naïve and therefore vulnerable - akin to a lamb going off to slaughter. I didn’t know the little nuances of being single such as; you don’t have to talk to a boring stranger at a bar for an hour if he buys you a drink, or you don’t have to give your phone number out just to be polite. Blind dates never made me nervous. I never worried that the guy wouldn’t call me for a second date; rather I worried as to how I could let him down without hurting his feelings.  I wasn’t in a hurry to find a “new husband,” as much as I was interested in having some fun and companionship. Each one of us has a unique history of dating both early on and after a relationship dissolves. It’s up to us to remember this because all these past memories, thoughts and feelings have shaped us.

Recall the difficulties that occurred in your last relationship.

I’m sorry to tell you, but you played a part in those issues, and unless you realize what it was, it’ll likely recur. There are always two sides to every story, find out what the other side to your story may have been by doing some self-reflecting and/or see a therapist.

Find out why you chose the person you married. Did you think he had problems that would change after you tied the knot? Did you see the red flags from day one? Were you a victim of someone with a shotgun forcing you to marry a crazy lunatic, or were you attracted to a certain trait or did he just not meet your expectations. My husband loved to gamble and took a lot of risks. From business decisions, to online poker, to driving recklessly at times, he loved to gamble. Years after he passed away, I realized that my boyfriend had those same tendencies. I had to accept him the way he is, and as the Billy Joel song goes, “I love you just the way you are.” Looking back at your last marriage or relationship, did you “grow apart,” and what can you do to make sure you “grow together” in the next relationship.

Close your eyes again –visualize what kind of person you want to be on a physical and mental level.

Are you that person? What can you do to become that image? One of my favorite Buddhist quotes is, “What you think, you become.” Make it happen! Go to the gym, see a shrink, get a new job, style your hair, and/or join a charitable organization and make your vision a reality. It’ll help your confidence level immensely. Men love confident, happy and independent women. You’ll have more power to choose the man rather than settling for who chooses you.

Create a mental list of people who can help spread the word that you’re ready to date?

People are not mind readers. Don’t assume that friends, co-workers and family members know that you’re ready to get back out there. They need to have seeds planted that you’re available, and it would be a good thing for them to fix you up with someone. I highly recommend that you try online dating or a dating service. You must find single friends of either sex to go out with. Don’t shy away from going out alone to the local bar, and making friends with the bartender. He can tell you who’s single and who’s married. He’ll let you know the truth about the guys hitting on you. I’ve had a married man tell me he’s single only to be outed by the bartender. Making “New” single friends and Keeping the “Old” married ones -like the Brownie Troupe motto goes - is one of the most essential parts to being single and happy. You’ll need to have a group of singles, so if one’s busy, there will be others to choose from. The new friends can help you with your passions or careers and other aspects besides socializing. It’s networking at it’s finest! I’ve connected with some fantastic women who’ve shared their friends with me. Forming new relationships with single women who’ve gone through similar life altering circumstances can be comforting and enlightening. You can also meet new single friends through charity and religious organizations. Social media sites like Facebook are also great resources for making new connections.

Picture yourself on a date. What do you look like?

Would you run a marathon without getting in shape both physically and mentally? Of course not! If you’re serious about finding a partner, you need to be prepared. Be confident about your physical appearance. Thankfully you aren’t competing with 20 something year old bodies - your competition is fighting gravity and aging just like you. Everyone has grey hairs and stretch marks. My friend Toni says, “Those are your natural tattoos.” You need to choose to either do something about the extra flab around your waste or embrace it. If certain things like discolored teeth and a few wrinkles bother you, sell some stuff on EBAY and you’re your teeth whitened and a shot of Botox. It’s worth it if it gives you confidence. As far as your mental state, therapy is the best present you can give yourself. There are agencies that have sliding scales if cost is a deterrent. The other easy solution to feeling great mentally is getting your natural endorphins going with an exercise regimen. Find something you love doing; running, cycling, yoga or zumba, and put it into your week as a high priority. The endorphin rush will help revitalize you, and put you in a great mood (at least for 45 minutes afterwards.) Use the Internet and watch videos on (here comes a plug) YouTube like The KarenLeePoter Show. Go to the library, there are whole sections on self-help.

Envision signing a contract to never date a married man.

Make this a rule and if you think you are vulnerable to falling for one, tell your friends and have them make you accountable. I have personally been victim to someone who said seven years ago that he was getting divorced, and is still married today. Another married guy claimed to have been a widower, until a mutual friend told me that she was alive and kicking. Unfortunately the world is full of married men preying on single women. Here are some reasons why being with a married man is a no win situation; you aren’t a home wrecker, you wouldn’t want that to happen to you, and he’ll probably cheat on you. You have to be number one and have self-respect or no one will respect you.

Create a list of dos and don’ts on first dates. Here are some suggestions:

Do be honest, be yourself, and look happy. No matter how bad your day is going, turn it around and be positively radiant. If you don’t think you look good, force a smile on your face. This will work wonders. Don’t allow text only conversations before a date. Talk at least once to make sure he’s legit. Don’t reveal too much about yourself before or on the first date. Do think of it as fun and not as a job interview. Don’t be negative. Nobody wants to hear about the hostility you have for your ex-spouse. Don’t have sex on the first date, unless you’re absolutely sure it’s the right thing to do. Do ask questions and listen to the answers. This will provide you with the information you need about his past and a possible future with you. Don’t drink too much. Do use good table manners, yes it’s common sense, but needs to be said. Don’t answer your cell phone unless it’s a necessity- if you need to have it with you, put it on silent. No texting either unless it’s an emergency. Do give good eye contact and warm body language. Do offer to pay for the bill or at least split it. Do remember to thank the person for the date no matter how it turns out Do be polite to the waiter or bartender. Your date is watching you too.

Be alert to RED flags on the first date. These are some actual statements - I kid you not:

“I want to be upfront with you, I had prostrate cancer and if we have sex, you’ll need to press a button on a penis pump that I wear.” “I would only date someone who can help me pay my mortgage.” “I won’t be able to kiss you tonight because I have a giant cancer sore in my mouth. I also am on medication for depression and anxiety.” “My ex is a c@*!t.” “I’m not working right now because I’m waiting for my Dad to pass away at which point I’ll inherit a lot of money.”

Plan your “How Stella Got Her Groove On” night ahead of time.

Only go to this step if you plan on being in a monogamous relationship. You deserve to be more than a one-night stand no matter how long it’s been since you last had sex. Don’t worry about being naked. Your partner will be naked too. Everyone is self-conscious and that’s why Thomas Edison invented the light bulb, and the dimmer switch to go with it. Wear sexy lingerie! Men are visual creatures, and the image of you in a teddy will linger long after this night. Speaking from past experience, test-drive the lingerie especially if it has a lot of hooks. I had a particularly stressful experience with “thigh highs.” Prepare for the night in advance. If possible set the mood with candles, massage oil, condoms, and get rid of the kids. A quick note about condoms - use them no matter what your partner says. If he says he hasn’t had sex in 20 years with any one other than his wife, wear a condom anyway.  If he says he was living in a monastery in Tibet, wear a condom anyway. Don’t trust anyone until you see the lab report that says he is clean. A friend of mine found out the hard way when a guy didn’t divulge that he had herpes.

Be honest with your partner about your fears and/or anxieties about sex. If you don’t feel comfortable talking about this, don’t have sex ‘cause you’re not ready. Communication is the key to having great sex. You don’t need to point out your C-section scars the first time, but you need to express any concerns that may prevent you from having an enjoyable experience. As your relationship progresses, you will need to feel comfortable enough to attempt different positions, role play or tell him/her what uniquely pleases you. This can only be done (unless he’s psychic) if it’s communicated. Please remember that things are different now than back in the hippie days. This means that you’ll need to trim the hair on your private parts. If you’ve never done it, you may find that it’s surprisingly erotic. Being clean and groomed will add to feeling sexy and confident.

Think about your sexual needs. Are you capable of having a “friend with benefits?”

Many newly single people go through a period of renewed adolescence. This can last anywhere from four months to 40 years. After being in a long-term relationship or marriage, being single can be lonely and one way to comfort yourself is through physical affection – simply put you’re horny and you want to have sex. Being able to have sex with whomever you want is a major perk to being single. This sudden unleashing of sexual restrictions can be liberating as long as it’s done safely. There are problems that can occur both physically and psychologically if you jump into sex without thinking of the consequences. Think about how you felt the first time you lost your virginity. A lot of the feelings of anxiety and excitement are similar when you pop your cherry the second time around. You may be more confident about sex now than at nineteen, but sex is still a very intimate activity and your feelings may get hurt as a result. I found this new found sexual freedom it be exciting, but on a few occasions depressing. A friend with benefits is all that you may want or can handle if you’re newly single. You may be so overwhelmed with your new life that anything more than a sexual relationship would be too complicated. If you have great sex with this person, you may end up fantasizing that this may turn into more. Friends with benefits may work, but you both need to be of a similar mindset. This is no easy feat, and communicating is key once again.

Realize the advantages and disadvantages of texting and sexting.

We didn’t grow up texting. Texting is much easier than having to pick up the phone or have a discussion in person. It’s also easier to be misunderstood and the problem is that once the text is out there, you can’t take it back. It sometimes ends up going to the wrong Adam or Kevin (oops.) I’ve personally read, and re-read a text several times trying to get to the deeper meaning, only to find out that there wasn’t one.

Sexting takes it one step further. Sexting is sending naked pictures or writing provocative texts in emails or on cell phones. It can be a lot of fun, and it also can get you into a lot of trouble. Sexting can give you a false sense of closeness since it’s easy to be brazen when you only have to press a few buttons. Be careful of what you send that can come back and bite you in the butt. If you send a nude picture and get into a fight with that person, you may find that photo on someone’s Facebook wall. I’ve seen this happen on at least two occasions.

Close those eyes one more time, and envision the person with whom you’d want to ride off with into the sunset.

What does he look, sound, or act like? Now open your eyes. If that person isn’t standing in front of you, it’s because he doesn’t exist. There is no perfect person out there. You need to come to the realization that the Prince isn’t going to come riding in on a white horse and sweep you off your feet. You are going to have to compromise (not settle) on what you want. If having great character is important, then you may not get the gorgeous multimillionaire. You may get the shorter than you’d like sweetheart of a guy. On the other hand, you should never accept a man because he has two arms, two legs and a penis. If you’re looking for a “Sugar Daddy,” you may not get a great companion. You may happen to fall in love with someone of a completely different religion, race or age. Try to think out of the box. Back to me: I’m currently dating a man who’s years younger than me. This was NOT something I was actively seeking when we met. Try to be open to being with someone different who you really click with and then go for it.