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I believe we can learn a lot from each other’s difficulties and accomplishments. I created the Ask Dr. Michelle column to share my advice with many people at the same time, who although they don’t know it, are often facing some of the same challenges. I hope that my comments provide you with some insight into situations that you are facing in your life. If you have a question that you want me to answer, submit it below. I wish you all the best. (I try to answer as many questions as possible, but please understand that due to the number of questions that I receive I am not able to answer every question.)

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How do I start dating again or be happy alone?

  • Question: I was in a serious relationship that led to me getting totally ripped off by this female and left me in a destitute situation. After two years of depressed states and trying to find good jobs in today’s market, I am finally getting back on my feet. Financially I am still in the red, but am on my way back to stability. I am gun shy about relationships now as well as I feel kind of inadequate due to the fact of my financial status. My question is, “When would be a good time to get back into the dating scene?” I miss having that closeness of a companion, but I am still kind of untrusting. Should I get back into the dating scene or be content with being alone?

  • Answer: How about a compromise?  You don’t have to jump back into the dating scene, but you don’t have to be alone either.  I don’t know if you have any female friends, but if you enjoy being in the company of a woman and can do so without pushing to make the relationship romantic, then why not spend some time with your female friends?  If you have a female friend, there is less pressure because she should have different expectations about what you do together.  Or, if you feel that hanging out with a woman is just too much like a date anyway, why not go out on a date but move really slowly, and by slowly I mean, at a crawl?  If you haven’t dated in two years I know you have had a lot of time to think about what you could have done differently in that relationship and what you will do differently in your next relationship.  These are important things to keep in mind as you move forward.

    Most people move way too fast in relationships.  If you are concerned about a woman really liking you for you, and her comfort with your financial situation, then you should take your time to just get to know her on a very friendly level, even if you want to reserve the right to make it more like romantic dating if you decide you really like her.  Don’t feel like you have to spend a lot of money to go out and have a good time with someone.  If you don’t know someone who would enjoy spending time doing less expensive things, then they are the wrong one for you anyway.  You shouldn’t bother dating anyone who makes you feel inadequate, especially when you know that you have been through something and that you are working to get back on your feet.    Try lower cost events like things that are free–you don’t have to promote the fact that it is free, but if it is and it’s still something fun to do then so what?  Where you live there may be free concerts, free movie passes, free days at the museum, etc.  You can also find cool places to eat that aren’t expensive but still have good food and atmosphere.  Try taking a walk or jog together, going to the park, renting a movie, playing billiards, or cooking the person dinner at home.

    You have to be creative but you don’t have to suffer alone.  Just move slowly and don’t expect too much.  Some people are not going to understand or appreciate your financial situation or your hesitation to get involved quickly, but don’t worry about that.  Let those people go their own way and don’t take it personally if they don’t see things the way you do.  There are many women out there so don’t commit yourself financially, practically, physically or emotionally until you take the time to get to know if they are even worth your time of day.  Once you meet the woman who you know likes you for you, and not for your money (and you will know because of how you interact and spend your time together) you won’t have to wonder about whether the time is right to start dating again.  You will be able to confidently know that she is the one to let into your life.

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