Social media have introduced many new, not always positive, wrinkles in dating. While Twitter is still largely the domain of the much younger generation, 20-, 30- and even 40-somethings sometimes find themselves at a loss as to how handle the prickly situations that arise as a result of Facebook.Add this to the laziness and lack of initiative and mystery – Why call when you can IM? Why not check out a gal’s plethora of pictures before committing to asking her out? – often reinforced by texting, and you have some thorny ground to cover.That’s not even taking into account the bad behavior of supposedly “attached” guys who use Facebook as a tool to relieve their boredom.Eva welcomes your questions about your most pressing dating dilemmas, as well as your feedback. Contact her at email@example.com. Please include your age and location; all other identifying information will be kept confidential.Not to worry. Here comes Eva to offer advice on your dating dilemmas! Dear Eva: I was recently at a Friday night meal and met a guy – like me, in his 30s and single. We really hit it off and spoke the entire time. Even his friend, who hosted the meal, made a comment about his obvious interest. At the end of the night, he said he would get in touch, which I took to mean he would ask me out.The next day, he sent me a Facebook friend request, but after that – nothing. Do I accept it and just wait for him to get in touch for real (i.e., an email, I guess)? Do I do nothing? Is he interested or not? Befuddled, R.W.Baka Dear Befuddled: I feel your pain – the situation is confusing. Given that you met at a Shabbat meal, it’s legitimate that he didn’t get your phone number, instead making a gesture on Facebook.However, a truly serious guy will not waste any time and will get in touch – but in a real way, and immediately. What he should have done was email you directly on Facebook and ask you out or, even better, write to you to ask for your phone number, then call you and invite you for a date. This ambiguous friend request is unclear and immature. He may be interested, but is hedging his bets until he can check out your most sultry profile photos and see what friends you have in common.The fact that he did not take true initiative is not a great start. But if you are not turned off (and that’s a real possibility), you can try to turn the situation around. Don’t accept the friend request and allow him free rein to check out your profile. Instead, email him directly and tell him how great it was to meet him, and that you’d be happy to talk some more. This is the opening for him to reply by asking you out.If he just replies that it was good to meet you as well or in some other noncommittal way, there’s your answer.If he does ask you out, great! But – there’s a but – while you should be willing to go out with him and give him a chance, keep in mind that he took a roundabout route to getting in contact. If he starts exhibiting more of that noncommittal behavior, consider it a warning sign and act accordingly.Dear Eva: I’m a single woman in my late 20s. Recently, a guy I used to be pretty good friends with when we were both single – he’s since married and had a few kids – IM’d me on Facebook. I had not heard from him in a long while, pretty much since his wedding.The conversation started out innocently enough but quickly morphed into his telling me that he’s really frustrated, since he and his wife barely have sex anymore. I just wrote “mm” and various other noncommittal responses, but he went on to teasingly ask who I was dating and if I was “having fun of my own/more luck than him.”All of this made me pretty uncomfortable. I know we used to be good friends, and nothing ever happened between us back when we were single – beyond one ill-fated date and some flirtatious banter. But shouldn’t his first loyalty be to his wife? Why was he so interested in what I’m doing? Or maybe he’s just looking for a shoulder to cry on? Mystified by the (instant) message, E.B.Motza Dear Mystified: Your gut feeling was right – the whole thing was inappropriate. In fact, being someone who believes that once a couple is married, there is no need to have intimate conversations with the opposite sex – especially someone who used to be in your social circle and you used to flirt with, however mildly – I would argue that the very act of IMing you was questionable.Judaism takes this into account, instituting a prohibition on yihud – a man and a woman, even a man of 19 and a woman of 72, who are not married to each other may not be alone in a room together. While I don’t personally follow this, I think the spirit of the law is right on: Avoid potentially compromising situations where there is even the tiniest chance something could happen.In the virtual world, things get a little murkier. It’s easy to argue that IMing just involves “harmless chatter.” But it also lends a false air of intimacy to the proceedings. Because you weren’t face to face, your old friend felt comfortable enough to confess very personal details of his marriage to you. If you were talking in person, say quickly catching up after running into each other in the produce aisle of the supermarket, do you think he would have inserted the little nuggets about his sex life? I doubt it. (All those heads of lettuce listening!) Also, I’m a big believer in living by the Golden Rule. If you were his wife, how would you feel if you found out your husband had confessed his dissatisfaction in the bedroom to a fairly random female? Pretty dang upset, I would imagine. Don’t let yourself be that woman.As for his inquiries into your life, I suspect he was trying to stir up a little excitement with someone he saw as a “swinging singleton.” Once he gets that information, he’ll either move on, having satisfied his craving for some insider info into the world of those with lesser commitments/responsibilities, or keep IMing you for further details.There’s nothing good that could come of this. He’s certainly not potential dating material for you, and you could risk developing an emotional connection that will hold you back from finding the right one, and cause all kinds of fallout for him.Bottom line: If he does IM you again, tell him the conversation makes you uncomfortable and suggest he speak to a trusted (male) friend, family member or professional. Then wish him luck and sign off. I would even recommend defriending him or, at the very least, putting him on limited profile.Don’t feel guilty about “not being there for a friend.” You’re doing him – and his wife and children – a favor! Good luck.Along these same lines: Dear Eva: I’m an unattached woman in my late 30s. I recently attended a wedding of a friend. Another friend introduced a distant family member of hers – who was married, his wife was there – to a group of us. I said maybe two words to the relative during this exchange. The next day, a friend request from the married relative popped up on my Facebook.I thought it was a little weird. It was pretty obvious I was single – or at least there alone.Or maybe he’s just being friendly and trying to expand his social circles? Klueless, S.T.Katamon Dear Klueless: In the immortal words of the movie of the same name (before it was “Kardashianed” with a “K,” i.e., Clueless): As if! Decline the friend request pronto! Did he send a request to the random male members of the group? I suspect the answer is no. But even if he did, a married man should not be friend requesting a single woman for any reason. Period.What kind of kosher interaction could you possibly have, should he truly be looking to expand his social circles? Would you get a cup of coffee? Go for a few drinks or an educational spin around the zoo? Or just IM? (See above.) Unless he and his wife share an account and he’s planning to include her in every conversation and potential outing, I can’t imagine that she would look kindly upon her husband’s new female “friend.”If he’s indeed looking to shake things up, I suggest he get a hobby. I hear birdwatching is lovely this time of year.