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The Little Red Book

The Six Month Mark

Are you feeling the stress of a long-distance relationship? Are you interested in someone who you consider to be out of your league and don’t know how to approach them? Join the club. Readers are going through those dilemmas and more, and Master Matchmaker Kristen tackles their issues.

Is it normal for a couple in a long distance relationship to argue about the distance factor? – Eliana

It is if all the traveling is one-sided or if there is no long-term plan to ultimately be together. You can’t stay long distance forever; it just won’t work in the long run. So it is natural for the distance to become an issue at some point. You should be working towards a common goal of coming together and sharing the traveling burden until then.

What is a good way to initiate a discussion about the future of your relationship? – Jose

Just do it! Find an appropriate time where there are no distractions to sit down with your girlfriend and tell her your feelings and ask her about hers. Compliment her and tell her how much you love being with her, spending time with her and look forward to your future. Don’t grill her for answers. Not all relationships are the same, but generally a good time to bring up your future is after being exclusive for about six months. You should have a good idea based on how the relationship is going thus far, but it is good to have open communication and never assume someone’s intentions or feelings. There is no point in staying in a relationship that is going nowhere so it is healthier to have the discussion and determine if you two have a future.

I have never been in a relationship before. What is a good way to build confidence and acknowledge someone without being awkward?  – Anthony

Smile and be nice! Don’t be weird. Find a common ground or topic that you can discuss with them that you can both relate to and just start with a friendly conversation. Keep the topic light and the conversation upbeat and fun. Once you have broken the ice, have spoken to her a few times and have developed a friendly rapport, ask her out on a simple date – a cup of coffee, a drink, a game of tennis, etc. Don’t go to the movies or plan a long extensive date, do something very simple at first.

What is the best strategy for asking someone out on a date who you think is out of your league? – Aaron

The answer to this is very similar to my last response to Anthony. Smile and be nice! Don’t be weird. If you truly feel she is out of your league she will pick up on it and not be attracted to your apparent insecurities. Be CONFIDENT! Women love confident men (not cocky… confident, there is a distinct difference). Strike up a conversation, be funny and make her laugh. Look into her eyes with confidence (but don’t be creepy and stare her down) and work into asking her out on a simple date. Assume she will say yes, don’t sell yourself short. If she is not interested you will know by her response.

Why do women mind so much when the “wrong” type of guy hits on them? – Nguyen

Most women (and men) don’t want to waste their time with someone they don’t feel is right for them. They should be polite, but it is better not to lead someone on if they are not interested.

Kristen Quackenbush is executive director of Client Relations with Master Matchmakers®. A high-end matchmaking service that has been connecting and coaching bright, attractive, successful single men and women for more than 20 years. She can be reached at Kristen@mastermatchmakers.com if you are looking for assistance meeting your life partner!

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