Dear Wendy: “Will Having Sex With My Boyfriend Ruin My Marriage?”

It’s time again for “Shortcuts.” For every question, I’ll give my advice in three sentences or less, because sometimes the answer to a person’s question is so obvious and the need to hear it so great, being as clear and frank as possible is simply the best way to go. Today we discuss whether sex with a boyfriend can ruin a marriage, the ethics of dating one’s lawyer, and reaching out to a friend you’ve wronged.

I have a boyfriend with whom I badly want to have sex. But there is no chance that I will be getting married to this boyfriend of mine. My boyfriend is not going to be my husband. I am afraid that having sex with my boyfriend would ruin my married life with my husband. But I really want to do it. Even he is desperate on doing it. It is me who has refused him. Please advise what should I do. — Sex-starved

Unless you’re already married to another man or come from a culture where premarital sex is strongly frowned upon and engaging in it would greatly jeopardize your reputation, there is no reason to fear that sex with your boyfriend will ruin your marriage. In fact, there’s a pretty good chance it would make it better as you’d have more experience and a better understanding what you like and don’t like. I say go for it, if it feels right to you.

My ex recently had some trouble with the law and is currently in jail for the crime he committed. It wasn’t my fault, but because the authorities were investigating me to see if I had any involvement, I got a lawyer. The problem is I now have a huge crush on him. He is my age, 30, and smoking-hot. I really want to ask him out, but: a) have no idea if he even likes me, and b) I think that even if he does like me it may be unethical for him to say yes. He is very flirtatious with me. He has even been over to my house a couple of times to have me sign paperwork after hours. I have talked to other people in similar legal situations, and their lawyers rarely even talked to them. Mine called at least twice a week and asked me to the office on a weekly basis just to check in. Whenever we talk we get way off topic. In fact, we have quite a bit in common. This is a guy that if the circumstances were different I would totally ask him out. I know he is single and available, but because of the professional nature of our relationship I am paralyzed. I guess this is kind of a multiple-part question. First, how do I confirm if this guy even likes me, second, if he does is it OK for me to ask him out. — Lover-in-law

There’s really no way to “confirm” whether this guy likes you before you risk getting rejected — that’s why asking someone out always takes some guts and confidence. I say if your professional need for him is just about over, say, something like, “Hey, even though the circumstances of us meeting weren’t the most pleasant, I’ve really enjoyed getting to know you and was wondering if, when I’m no longer a client, you might be interested in going out sometime.” His answer will tell you everything you need to know.

I have been seeing this guy for about two months now. We’re both in graduate school (I’m going for my master’s, he’s in law school), and are incredibly busy. We spend a lot of our time together at the library during the week, and on the weekends usually grab a drink or two together, or just hang out and watch movies. When I asked him about where we stood in our relationship, he avoided answering the question. I brought it up again, and he just said that he “doesn’t really do the girlfriend thing,” but that he is comfortable with where our relationship is right now, and doesn’t feel the need to change it. Where we are is fine for now, since we’ve only been seeing each other for two months, but I’m worried that he won’t want to make me his girlfriend ever. What should I do? — Lost in Limbo

He basically told you he’s never going to make you his girlfriend when he said he “doesn’t really do the girlfriend thing.” There’s nothing ambiguous about that comment at all and if he wanted to leave you with the impression that there could be an opening in the future, he would have chosen different words to convey that. If you aren’t content having him as basically a friend with benefits and don’t want to invest more time in a relationship that doesn’t have much of a future, be honest with yourself and with him and MOA.

About three years ago, I had a best friend. We spent almost every day together: we would go out to parties, out to eat, meet boys, etc. One night, we were drinking and when she wasn’t around, her boyfriend at the time made some moves on me. Being a bit intoxicated, I kissed him back, and he started initiating more. I did stop it before it went to far, but still I felt awful. She found out (from her boyfriend) and specifically told me she didn’t want want to hang out with me anymore. She wasn’t mean about it — she just said that I wasn’t the kind of person she wanted to be friends with. I apologized, told her I understood, we said goodbye and that was it. I didn’t hear from her again. She went off and joined the Army, while I did my own thing. We remained friends on Facebook, and over the past few months she has been commenting on my status and photos pretty regularly. They have all been nice comments, and I started returning the favor and we seem to have a somewhat regular “Facebook friendship.” I really miss her; she was such a good friend. I know I messed up and I have never again done that to anyone no matter how drunk I was. Before that event, we were friends for almost 5 years. Now, she’s heading back to town for the holidays and I really want to see her but I’m scared. I don’t know if I should reach out and make the effort, or just leave it be and if she wants to see me let her say so. Is it worth making the effort? Or would I come across presumptuous in assuming she would actually want to be friends again? — Missing A Friend

Absolutely reach out to her! Tell her you know she’ll be busy seeing family and friends while she’s home, but if she has any free time at all, you’d love to get coffee and catch up in person. If she’s not interested or ready to see you, she can always claim she’s too busy without hurting your feelings or making things awkward, and if she does want to see you, you can tell her in person how much you’ve missed her and how good it is to see her again.

Follow me on Twitter and get relationship tips and updates on new Dear Wendy columns!

*If you have a relationship/dating question I can help answer, send me your letters at {encode=”[email protected]” title=”[email protected]”}.