Q: Dear Amy, I am a divorced single mom of 1. I haven't dated in 3 years by choice due to a traumatic breakup and legal battles that have taken a toll on me. In the past, when childless, I was able to quickly regain my confidence and date easy after a breakup, but now I am feeling a bit tense and afraid as I feel that after the last relationship I might have been "damaged" somehow, in addition I have just been diagnosed with Vitiligo that is affecting all soft tissues in my body (lips, nipples, genitals)...

I am scared to jump again in the dating pool, so I have started to workout regularly, and signed up for online dating where I seem to have a lot of success. You see, there are several men that I am interested in and for now, I'll keep it at that; just emailing. However 2 of them, whom I really like a lot, are already asking about meeting me and coming to my city. I am at odds at what to do, I don't feel totally ready for face to face meetings. I am good looking and fun, but I still feel something is off... could it be I am just out of practice? Would you please help me? Thanks, Unsure beauty

Amy: Dear Unsure Beauty, Your hesitation and uncertainty around dating sound completely reasonable and normal to me. Going through some painful episodes in your personal life and dealing with a disorder that shakes your confidence are big things that would make most people anxious about dating.

I think your approach is great. Working out and doing anything you can to build your confidence for yourself, then gradually meeting people online or in a safe, slow setting, is ideal. About meeting these new guys in person…I'd say that if you don't feel ready, wait until you do. Sure, you run the risk of moving too slowly and may get impatient and move on, but if you meet them before you're ready you could feel the need to back off and end things too. Either way, things may or may not work out but by waiting until you feel ready at least you are doing what feels right to you.

Having said that, you may want to think more about your fears about meeting these guys and evaluate if those fears are really valid and what you may be able to do to diminish them. For example, if you have a fear that they will be disappointed with your physical appearance, you might share more pictures or talk to them about your Vitiligo so that you can go into your first meeting feeling more comfortable. I would recommend that you make a list of the things you fear about dating. You can play out each of those fears in your mind and take an objective look at how likely they really are (hint: they are NEVER as likely as we imagine them to be). What would be the worst case scenario if that fear did come true? Why would that be so bad? When you really think about it, the worst case scenario is often that the relationship doesn't go any further. Is that really so bad? It can also help to talk about some of your fears with a friend or a coach who can offer a different perspective.

Don't be so hard on yourself for not being ready. Just take it at whatever pace feels comfortable for you and do what feels right each step of the way. If you continue to feel very stuck and afraid, write down some of those fears and do what you can to work through them. Good luck!

Q: Dear Amy, I have been too busy with my life, focusing on my career and raising kids as a single mother to have time for finding a significant other in my life. I feel like I have lost touch with that part of my life. I now want to make room for a significant other now that my kids are grown up and I have more time for myself.

But, I feel that a part of me is holding me back maybe because it has been a while since I have met someone. Please advice. - Irene

Amy: Dear Irene, dating is just like anything--the more you do it, the better at it you get. You're just a little out of practice. Take it slow, meaning don't schedule 4 dates for next week. It may help to get to know just one person at a time and explain to that person upfront that it's been a while since you've been in the dating world and you really want to ease in to it. Finding someone who wants to see you four or five days a week from the beginning is enough to make you abandon it altogether, so make sure the people you date understand where you're coming from and are okay with moving at a speed you are comfortable with.

You say that part of you is holding back...I'd like you to make a list of all the reasons you either shouldn't date, or fears you have about dating again. When you have that list, go item by item and ask yourself, "Is this true?" "Can I know for sure that this is true?" If you need to, provide evidence for why the fear is not true. For example, if one of your fears is that you will waste your time dating the wrong person because you haven't dated in a while, ask yourself, "Can I know for sure that this is true?" If you think about it, I suspect you'll find that it could be true, but it could just as easily be totally false. Fears are basically just stories that our brain makes up, usually based on very little or very skewed "evidence". I tell my clients that F.E.A.R. stands for False Evidence Appearing Real. You can also come up with some evidence to support why your fears may not be true. In this case, you might think, "I am usually a very good judge of character", or "Even when I did date regularly I could usually tell if someone was the wrong person for me". There may be a lot of evidence--all of that helps the fear dissolve away. (By the way, you can use this method with fears about anything, not just dating!)

I don't know if this is the case for you, but often times single mothers who haven't dated for a while worry about how their kids will react, or how men will react to their children. Give this some thought before you jump in. Do you want to introduce your kids to your dates? If so, how soon? How will you approach the subject with your kids? What concerns might they have and how can you address those? What is important for your dates to know about your children, lifestyle, priorities, etc.? Going into your first dates with many of these issues thought through will ease a lot of anxiety and help you focus on the moment. Good luck!

Q: Hi Amy, I recently met this woman I really like, who also happens to be a single parent. I would like to engage a relationship with her but I have never dated a single mother before. I am wondering if you could give me some advice on how to make this relationship work for the both of us? – Vivek from Los Angeles

Amy: Hi Vivek, Entering a relationship with a single mother can be quite a change, especially if you've never ventured into this territory before. It's great that you are thinking ahead and trying to formulate a plan to assure that things go as smoothly as possible.

I would basically ask her exactly what you asked me. Tell her that you've never dated a woman with children before and you'd like her perspective on how to best make it work. You can ask about her experiences dating men who don't have children; if she's been dating for a while, she's likely been with some guys who've handled the situation well and some who have found that it wasn't for them. What does she think makes the difference? If you have specific concerns, go ahead and voice them. For instance, you may have questions about the children's father, or how she feels about introducing her children to her dates. If these things are on your mind, it's more than okay to ask. I've found that one of the best things about dating people with kids is that because they've experienced more in life than your average person, they're typically more willing to put everything on the table and be open and honest from the beginning.

When should you begin this dialogue? That kind of depends on how your relationship progresses and her openness about her family and dating situations. If things start off strong and she appears to be very open about her lifestyle, it may be okay to have these conversations as early as the first date. If things progress a little more gradually, perhaps the third or fourth dates feel better. It's different in every situation and really comes down to what feels right to you.

Telling her that you've never been in this situation and asking for her help also shows her your level of maturity and dedication to making a relationship work--both very good things to a woman whose first priority is providing a safe and stable environment for her children. Good luck!