A. These questions are tough to answer because… Um, he wants sex. You’ve presented me with a bit of a puzzle here and I’ll have to do my best to draw some conclusions.

You were with the same guy for 13 years and you’re now “on the dating side again which you never did”. How can you be on the dating side “again” if you never did date? I’ll conclude that you have no dating experience. You stated that “he wants to go farther” and “now he’s asking”. I’ll conclude that he’s trying to convince you to go to bed with him. If my conclusions are wrong, you can straighten me out another time.

I answered part of your question in the first sentence. Yup, he wants go to bed with you. I’m not sure what else he wants but based on the laws of probability, I’d say all he wants is the sex. It’s nice that he played cards with you until 5am. It’s amazing what guys will do when they first meet a chick to impress them and try to go to bed with them. Men are resilient creatures when it comes to this. We’ll stay up until 5am talking, go for a walk in the rain, watch stupid things like figure skating on TV – just to impress. I once agreed to take a woman skiing and I’ve never been skiing in my life. But back to you and the point of view you asked for…….

Some people are cut out for the dating scene and some are not. Either way, I have 2 words for you – don’t settle. Don’t settle for the first guy who comes along, don’t settle for someone who’s just OK, and if you want to get married someday don’t settle for a guy who only wants to date you for 13 years. I’ve got two more words for you – be patient. If this guy wants to go “farther” with you and he really likes you, he’ll wait until you’re ready. If he gets frustrated after a week or two and leaves, that will tell you he only wanted sex. After 13 years with the same guy I’m not sure if you want a serious relationship or if you’re currently looking for an all you can eat man buffet open 24 hours 7 days a week. Either way, it’s all out there for you.

My conclusion is for you to enjoy your new friend, have a ton of fun meeting guys and most important: Be Patient and Don’t Settle.


Q: My boyfriend and I just celebrated our 4th anniversary. I still don’t have a ring on my finger. Should I move on or give him more time?

A: I hear this question a lot. Chances are if you’re asking the question, then you know the answer. You’re just looking for someone to validate your decision to move on. Let’s see if I understand the facts as they’ve been presented, you’ve been with this guy for 4 years, you want to get married and you don’t have a ring. Did I miss anything? Have a discussion with him. Tell him you’ve done your time and want to get married someday soon. If he blows you off or he can’t give you an indication as to when he’s going to ask you, then tell him you want out of the relationship. Hopefully you’re not dating some mobster from NJ. If he really wants you, he’ll fold like a cheap suitcase and ask you to marry him. It might take a couple of months, but he’ll come crawling back with a shiny ring. What if he doesn’t come back? Then you know he wasn’t going to marry you and you’re back in the game. Either way, you’re going to get your answer quicker by confronting him with a conversation and taking appropriate action afterwards. If you’re a cutie, send me an email with a pic because I have single guys in the club and I’ll see what I can do.

Q: I just broke up with my boyfriend and have been out of the dating scene for a while. What are the best ways to get back in the game? Is the internet dating scene safe?

A: Welcome back – let the games begin. Friends and family are always the best way to meet guys if you’re patient. The friends and family plan can be frustrating because it’s like you’re in a giant lab experiment, but you’re getting a guy that’s got a built in approval rating. If you’re a bit outgoing and non-traditional, you can hit the bars and flirt with any guys who offer to buy you a drink. If a guy offers to buy you a drink and you like him, make sure you give him your number or email before the night is over. I don’t know why chicks don’t pick up on this more. If we smile at you, talk to you, buy you a drink – you’re in. Internet dating is anonymous and as safe as you want to make it. The thing about internet dating is that it’s a quantity driven service not a quality driven service. You’ll get a ton of odd balls, pigs and serial daters emailing you once you post your profile and a few decent, serious men. Only respond to guys that post their picture – don’t waste your time with guys that don’t post their pics or even with the ones who offer to email you pictures. Hint: married guys and guys with girlfriends do that. After a few emails, talk on the phone before you meet – See if he can hold a conversation. If the call goes well, set up a date at a time and place you feel comfortable. Be ready for a potential shock. There’s something I call “online chemistry” that you can develop with someone via email and the phone. That online chemistry can be shattered in a fraction of a second when you meet them in person. Also, be prepared to meet guys that do not represent themselves honestly. The biggest complaint I’ve heard from women is that the guy doesn’t look like his pictures. Some guys will use pictures from 10 years ago or someone else’s pictures all together. Always ask how old the pictures are when you first start to email. If you’re looking for a great boyfriend and a guy you want to marry, don’t settle – keep your standards high and know what your “deal breakers” are. On the other hand if you want to date around, there are plenty of the aforementioned odd balls, pigs and serial daters for a woman on the loose.

You can email questions to Milo at
asktheexperts@undercoverwear.com