Questions of Time

I dated a guy in college and we reconnected ten years ago, both of us in relationships. We built a nice friendship over the years and now both of us are single. We’ve hung out a few times recently and there was definitely a spark, but I’m afraid to pursue it because I don’t want to screw up the friendship. It’s always a risk when converting a friendship to a “love-ship”, but it doesn’t necessarily have to end in tragedy. Continue spending time with him and let nature take its course. Communication in any relationship is key, and communicating your desire to never compromise your friendship will most likely be met with resounding agreement. If you mutually want to test the waters, agreei

I Do, I Don't, I Might

My partner’s brother is getting married and considering how his family isn’t friendly towards me nor are they accepting of our relationship, I wasn’t surprised to be excluded from the invitation. Sure, it sucks for me, but it really sucks for my partner. He refuses to go to the wedding if I’m not welcome. Is that the right choice? It might be the right choice for him- it’s his call to make. I see where you don’t want to be the reason for fallout between your partner and his family, but you should remember that this isn’t about you- it’s about his family accepting him and the life he’s living. Support his decision either way, and let the chips fall where they may. As a strong couple, yo

Collateral Damages

I’m a year into single life after my breakup and I just started dating again a couple months ago. On the dates I’ve been on I’ve noticed that they always bring up their Ex in the conversation, leading to them questioning my breakup and telling me all about theirs. Why do people always bring up their Ex on first dates? Unless they’re on probation for attacking or stalking their Ex, you really don’t need to know anything about the past relationship of your date this early in the game. A first date is suppose to be a tool to get to know a new potential love interest. Hearing all about their Ex defeats the purpose and is a sign that their Ex is still on their mind. Maybe they’re not over th

Shirting, the Issue

I’ve been dating a guy for six months and at the beginning of our relationship he always looked great when we’d go out. Lately I’ve noticed his sense of style is going downhill fast. Instead of always looking crisp and put together, he’s now sporting dirty jeans and T-shirts whenever we go out. How should I handle this? Have you tried pointing out that he looks really, really casual for a dinner date? If he says that he wanted to be “comfortable”, remind him that he can still be comfortable in a nice button down oxford shirt. Try reminding him before the next date that you’re going to a nice place and he needs to kick up the wardrobe a notch. If that still doesn’t work, have a conversa

Congregation Trepidation

I’m trying to take your advice and meet new potential dates in real time situations. My problem is that when I’m in a bar or at a party and I see someone I think is cute and available I’m too afraid to make the first move. How do I overcome this? How? You just do it. Here’s why… When you go into a real time social situation, you’re alone and without any prospects. By not making the first move, you’ve increased the odds that when you leave the social situation you will do so the same way you came in- having zero potential dates and still alone. There’s nothing to lose by making the first move; there’s only a gain. If you try and nobody takes the bait remember that even the most seasone

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