Q: I am seeing a woman that is going through a divorce (he is in the same house and knows) and has 2 children. I am 52 and she is 44. I have known her since she was 9 years old (brothers friend). We dated briefly when she was 25 and we parted. She found me again a year ago. I could tell in our first conversation that there was more and we fell madly in love almost immediately. We have been best friends since day one. I only get to see her two days a week mainly on Thursday and Saturday. We talk on the phone 4 - 5 times a day. We are very close and get along well. I feel that she is my soul mate and future wife. Her soon to be ex had erectile dysfunction for two years and she had asked for a divorce a year before this relationship started. I have never had a problem with sex until now. She has been critical when i didn't perform or have been tired. At times we don't seem to click or reach point of satisfaction together and am not sure why. I just have a problem with being insecure in this relationship and fight it. I have a good job, home and have always been secure. What do you think could be affecting us? What should i do to correct this insecurity?

Amy: Dear Bobby, It seems like quite a coincidence that your sexual issues and insecurities began (or are at least highlighted) in this relationship where she’s coming out of a marriage affected by sexual dysfunction. You see the connection, no?

Of course I don’t know for sure, but it might go something like this: She is hyper-sensitive to sexual issues given her recent past and her sensitivity makes her critical of your performance. You are also sensitive to sexual issues on some level just by virtue of knowing what she’s been dealing with. Your sensitivity, combined with her added pressure and both of you fearing that there might be a problem in this relationship, causes problems when they do occur. Your insecurities grow with each sub-par encounter, and it turns into a vicious cycle. So your question about correcting your insecurity is part of it, but its likely more complex than that.

If any of this resonates with you, I’d start by having a talk with her about the situation to get her take on it. Does she think that her issues with her husband might be affecting the way she reacts to you? Could the two of you work together to keep the situation with her husband and the situation with you separate? How could you respond in a way that would make her feel more confident and secure, and vice versa?

This conversation would be a huge step in the right direction and very often all it takes to make an enormous difference. Because the pressure and fear of things going wrong in bed is what actually contributes to things going wrong, getting the issues voiced and out in the open relieves a ton of pressure. Good luck.

Q: Hi Amy, I am in relationship with a guy for last 3 yrs. I really want to break up as I feel smothered in this relationship, but have past unsuccessful attempts. the maximum time period was 2 mn and I again go back to him. Its a long distance relationship. I keep telling him repeatedly that I am never going to marry him but I am not able to date any one till I am in talking terms with him. He is a very persuasive guy. everyone around me just says that its I who have to be strong to break up this relationship else I will ruin my life. I feel that I need some support and constant encouragement to do this. Is there any help available in terms of support when you go through the loneliness period and prevent me from falling back to him. - Purnima

Amy: Dear Purnima, When someone tells me they feel smothered in a relationship yet they keep going back time and time again, there’s a lot more going on than can be addressed in a few paragraphs. The ultimate question is: What’s so bad about being alone? If you’d rather be with someone who smoothers you than be without him, you obviously have some issues with being alone.

I want you to look very carefully at the thoughts that come up during that “loneliness period” that makes you go back to the relationship. Loneliness is the emotion, but what are the actual thoughts? What are you telling yourself during this time? You are telling yourself something that makes you want to go back to him, something that makes your feeling of loneliness feel much worse than being in a bad relationship. Your first step to changing things is to identify those thoughts so that you know why you keep going back.

Once you understand what it is that scares you so much about being alone, you can deal with it. I recommend you talk to a friend or a coach or therapist about those fears if they feel too overwhelming to handle on your own. The most important thing to keep in mind is that those fears are most likely not true.

If you need support in the time right after you break up, try to find it in a friend or family member who will agree to be there for you. Tell that person up front that you keep falling into this pattern and you’d like them to remind you that you don’t want to be with this guy, even when you get lonely and feel like you want to go back. You might also write yourself a letter that you can read during that period. Write the letter now, during a time when you are confident that you don’t want to be with him so that in your lonely period you can read it to remind yourself of the bigger picture.

Q: So I'm 25 and never dated, problem is I thought by now I would have my own place but life didnt work out, big problem is I feel I can never bring a girl to my house to meet my parents, my mom is into religion real bad and tries to force it on everyone and my stepdad is sort of the same way he bitches about everything and just doesnt stop then goes to church and pretends to be good, I'm not religious at all And cant stand living here but dont make enough to live on my own or with friends my job has cut hours so bad I'm working 12-15 hours a week been trying to find anything but no ones hiring where I live or so it seems, i was always waiting until I had my own place to date but doesnt seem like its going to happen even my friends have told me not to bring a girl over to my house, i have to actually go visit them because my parents get on there nerves, talking with my parents isnt an option anyone have any ideas how to fix this situation or do I have to wait until I get a job and get out of here? - Jon

Amy:Dear Jon, I understand your living situation, but what does it have to do with dating? You don’t have to bring girls back to your parent’s house if you aren’t comfortable with it. In fact, from the way you describe it I agree that you probably shouldn’t bring them there. But why would that prevent you from dating altogether? You can still take a girl out to dinner, to the movies, to her place…There are an infinite number of possible places to go and literally one place that you can’t go. I don’t see the problem.

I think you're using your living situation as an excuse to not date. Often when people wait for the circumstances to be perfect before they act, they’re really just avoiding action. I don’t see any reason at all that you can’t begin to date and just not take girls to your home. If you find a girl you really like and you go out with her several times and she asks about your living situation, tell her. You have to be honest about your family at some point whether you live with your parents or not. But that’s about five steps down the line and not something you need to worry about today, if ever.

Stop waiting for the all the stars to align and for everything to be perfect, or you’ll find yourself waiting forever. You need to start dating and take it one date at a time. There’s no reason to rush ahead into, “what happens after a month when she wants to see where I live?” Just start at the beginning and ask a girl out first, before you jump into imaginary future outcomes. They are likely not as scary as you imagine.

Q: I have been dating my boyfriend for about 4 months. I know he really cares about me and vice versa. He has just started studying for the bar exam and he is also taking classes. He also found out last year in December that his father has terminal cancer. He is an only child and I know he is going through a lot. I want to be supportive and I see a future with him. but I need to know what to expect from him. In regards to affection, attention, phone calls etc. I know I have to not take things personal but how much "neglect" is ok? like where do I draw the line? Also how can I make things easier? Should I just back off? like if I don't hear from him all day, should I call him? or should I just let him be? I don't want to push him away but is it wrong to also think about myself and what I need? - Arpi

Amy: Dear Arpi, It’s not wrong to think about your own needs and this is the perfect opportunity to evaluate them. Take a good look at what you want and what you’re willing to compromise for this relationship.

As far as what he’s going through, I wouldn’t expect much from him or from the relationship right now. I think the best thing you can do is to be there for him and approach this as if it’s an opportunity for you to help. If you feel comfortable with it, make this relationship about serving him and helping him through this time. It’s okay if that doesn’t sound like something you’re up for. That’s totally understandable, especially considering that it’s only a few months into your relationship. But if you are up for it, constantly ask yourself how you can best support him. Many times that’s going to mean asking him that question and doing what he says even if that’s giving him space or setting aside your own needs for his. Remember that this is temporary and things will even out if you’re together long term.

My hunch is that you may not be in a place to give up your own needs for him at this time. That’s not a bad thing and it doesn’t mean anything negative about you. It could just be that it’s only been 4 months and you aren’t sure about this yet. That’s totally okay. If you aren’t up for it, be honest about that with yourself and with him. He will understand. If you really feel that his issues being priority right now isn’t what you want, it’s okay to admit that to yourself and take a step back from the relationship.

I can’t answer your questions about when it’s time to call and when it’s time to give him space. Those things depend on him and his preferences, so you need to ask him those questions. Just ask—he’ll likely tell you exactly how you can best help him. Make sure to listen with an open mind and remember that it’s not about you. He’s dealing with major life issues and he deserves to do that drama-free. If you fear that you may start to resent him for neglecting your needs, talk to him about that upfront. And if, despite open communication, you begin to feel neglected or like your needs aren’t being met, take a break from the relationship and let him go through his stuff without you. His life will settle down and you can try your relationship again at that time.

Q: My girlfriend in college and I dated for 2 years before breaking up, we recently found each other again and were together for 1 year before she ended it saying I don't spend enough time with her and that she needs to travel and find herself. I am currently in medical school and before we reunited I tried to explain how difficult it would be to have a relationship due to my time constraints. She said she understood at the time and was always there for me, but over the course of the year she felt more and more used as our relationship had to live around my schedule. She resented me always putting school before her and I resented her not understanding my commitment. Well 2 months ago she ended it saying perhaps we can meet up again in the future as we did this last time. She is planning on traveling west with a friend of hers and will perhaps try to find a place to live out there. I am beside myself now with guilt for having let this relationship fail a 2nd time. I truly love her and I feel she loves me, there just seemed to be too many forces pulling us apart. I am nearing the end of school now, things have died down and I have free-time, all I can think is I wish she was here. She leaves soon for her trip and I don't want to lose her, but I know this is important to her. How should I proceed? Should I just trust in fate to reunite us? Next year I match for residency and I wanted her to come with me, but she says too little too late last we talked. Please help. - Will

Amy: Dear Will, Yes, I think you should definitely trust in fate to reunite you as it did in the past because it’s a no-lose solution. When you believe that things will work out for the best without your needing to control the details, you win. No matter what happens. You win because you give yourself permission to not worry. When you aren’t worried, you not only feel good in the moment but you free your mind to see other possibilities and creative solutions that you just don’t see when you are consumed by anxiety. So, trusting that everything will work out if it’s meant to—and reminding yourself that it happened in the past—are excellent things to do.

Trusting in the Universe doesn’t necessarily mean giving up all action. You can have complete faith that things will work out and still take action when it seems appropriate. In this situation, it sounds like the ball is in her court. I would suggest telling her exactly how you feel without any agenda or hopes of changing her mind. As much as you want her back, I’m sure you’d agree that the most important thing is that she’s happy. If she decided to give your relationship another chance but wasn’t totally on board with her decision, neither of you would win. The choice to try again has come from her and it has to be what she really wants.

Tell her how you feel and that you’re afraid that you may have lost her forever. Let her know that you are there when she’s ready to talk and that you’d be thrilled if she decided that she wants to try again, but that you want her to do what feels right to her. And then really set her free to do what she needs to do. If that means traveling or even living somewhere else for a while, trust that she’s doing what she needs to do in order to ultimately do what’s best for both of you. You can use any time apart to your advantage as well, getting reacquainted with yourself and your desires after the grueling years of medical school. Get back in touch with what you enjoy, renew friendships and build new ones, and focus on having fun for a while. If she felt as though school came first in your life, it probably did. Put fun and play first for a while and see how things turn around in your life.

Often, the circumstance that’s causing your relationship stress might just be a trigger for deeper issues. You say that she resented you for putting school first and you resented her for not understanding. Know that if you were to get back together, even though the external circumstances may have changed, your resentment issues might come up over some other circumstance. They may not—but it’s something to think about and possibly discuss if you do end up giving it another shot.

Good luck. I know it’s hard to be the one waiting. The more freedom you give her to do what she needs to do, the better your chances of reconciliation.